The Bossticks - Dee Ocleppo Hilfiger On Balancing Family, Fashion, A Lasting Relationship, & the Business of Living Well

Episode Date: October 30, 2025

#901: Sit down with Dee Ocleppo Hilfiger – former model, visionary designer, entrepreneur, & philanthropist. Known for her effortlessly sophisticated style & attention to luxurious detail, Dee creates designs that empower confidence & individuality. In this episode, she shares her journey from modeling & Wall Street to leading as a creative director & entrepreneur, including revitalizing Judith Lieber with viral designs & launching her own brand, DO by Dee Ocleppo. Plus, get an exclusive look at the iconic Hilfiger Homes, her secrets to a thriving marriage, & how she collaborates with Tommy Hilfiger on design & vision.   To Watch the Show click HERE   For Detailed Show Notes visit TSCPODCAST.COM   To connect with Dee Ocleppo Hilfiger click HERE   To connect with Lauryn Bosstick click HERE   To connect with Michael Bosstick click HERE   Read More on The Skinny Confidential HERE   Head to our ShopMy page HERE and LTK page HERE to find all of the products mentioned in each episode.   Get your burning questions featured on the show! Leave the Him & Her Show a voicemail at [phone].   To learn more about Dee and shop DO by Dee Ocleppo visit https://deeocleppo.com.    This episode is sponsored by The Skinny Confidential For a limited time shop 20% off our non-toxic clean candle at http://bit.ly/4nuyHLZ.    This episode is sponsored by SYNERGY Ready to get started on your very own gut health journey? Visit http://SYNERGYDRINKS.com to find your SYNERGY flavor today.   This episode is sponsored by Branch Basics Shop Branch Basics in 600+ Target stores nationwide, or http://Target.com. You can also use my code SKINNY15 to get 15% off at https://branchbasics.com/SKINNY15.   This episode is sponsored by Clarins Available at Ulta, Sephora and on http://Clarins.com.   This episode is sponsored by Just Thrive Visit https://justthrivehealth.com/discount/TSC and use promo code TSC for 20% off your first order.    This episode is sponsored by Bon Charge  Just head to http://boncharge.com and your 25% off code will be automatically added to your order.   This episode is sponsored by Square  Get up to $200 off Square hardware when you sign up at http://square.com/go/skinny!  Produced by Dear Media

The following podcast is a dear media production. She's a lifestyle blogger extraordinaire. Fantastic. And he's a serial entrepreneur. A very smart cookie. And now Lauren Everts and Michael Bostic are bringing you along for the ride. Get ready for some major realness. Welcome to the skinny confidential, him and her.

Today we're sitting down with someone who I really admire that I really enjoyed talking with. and that is Dee Hillfigure. She's a former model, a visionary designer, entrepreneur, and philanthropist. She is married to the one and the only Tommy Hillfigure, and she's known for her effortlessly sophisticated style, which you guys have to watch the YouTube because she's wearing the cutest outfit from her own brand, D.O. by D. In this episode, you'll get an exclusive look at how she thinks about designing her iconic Hillfigure homes, her secrets to a thriving marriage, and how she collaborates with Tommy on designing the vision. And you should also know that she is a busy mom. She has seven kids. She really does it all. Dee Hilfiger, welcome to the Him and Her show. This is the skinny confidential, him and her.

So happy we made this happen. Yes, finally. It's been three years in the making. Yes, it has. First question dive in. I think people look at your life and they think, wow, so, lucky, so easy, but it wasn't always like this for you. And I think a lot of this episode is around how you got here. So maybe to start, how did you get here? Well, I mean, that's a loaded question. It's been a long journey. I don't know how far back you want me to start. Do I go back to my Dallas days? Sure. You know, it's a long story. You know, I basically, my life, you know, I had a whole life before I met Tommy. Before I met Tommy, I was married to an Italian tenant. player and I was living in Monte Carlo and I was married with my husband for I think it was

maybe eight years, nine years and I wound up divorcing in 2003. I had two sons and I had been divorced for for three years when I met Tommy and I met Tommy in the south of France. Like I said, I was living in Monaco and he came to Centra Pado visit. And that's where we sort of met and became, I would say we were friends at first because we were living on different continents. And so obviously when that relationship bloomed, you know, my life changed a lot because I moved continents. I moved to where he was.

And then, you know, my life changed. But before I met Tommy, I had, you know, I was a mom. I had, prior to marrying my ex-husband, I had modeled. I lived in Paris. and when I stopped modeling, I actually came to New York and I was working on Wall Street at Prudential Baysh as a commodities assistant trader. So, I mean, I kind of feel like I've had maybe 10 lives, not even nine. I've, you know, I've bounced around. I've done all kinds of things. I've traveled many different places and, you know, landed here. Here I am. What was it like to live in

Monica. Well, I mean, it was, you know, I think from the outside, it like seems very James Bond and very glamorous and it was, but basically, you know, I would drive my kids to school. I drive them to karate. It was kind of like living, you know, any, any other places, very, very small. You live in, you know, you pay a fortune to live in a very tiny apartment and that part of it I didn't like. So eventually we moved just outside to Rock Bruins so that we could have like a bigger. house and, you know, with the kids, we just needed more space. And it's small and you kind of know everybody. But as a base, it's great. My kids grew up speaking two languages, or three languages, rather. So they, they're fluent in French, Italian, and English. So that was great.

It's safe. So, you know, like any place, there's good and bad. And how did you grow up? And I'm assuming you grew up out here in the States. Yeah. I grew up in Rhode Island, in East Greenwich, Rhode Island. My parents both immigrated. My father is from Istanbul, Turkey. My mom is, she was born in Birmingham, England, but then moved to Canada. So they actually met in Canada. And, you know, I grew up in a small town in Rhode Island.

And, you know, I had one sister. My dad was super strict. Really strict. What super strict looked like? Could never go to boy girl parties. I couldn't do basically anything. anything that all my friends were doing. Taking inspiration from your dad.

But I wouldn't because that made me, you know, very restless. And that's part of the reason why I... The tennis pro in Monaco. Okay, I got some... I'm tracking it now. I wound up going to Dallas where, you know, boy girl... I went to an all-girl Quaker school. Quaker?

Yes. So I had a very strict, you know, imagine like Turkish, English, Quaker. You know, when I got out of that and I couldn't sort of wait to get out of Rhode Island. I was looking for like, where is the farthest place I can go? When I finally got to Dallas, it was like very liberating and I had a lot of fun. Good for you. You have impeccable taste. Have you always had such a point of view since you were younger? Well, thank you for saying that, by the way. I don't know. I have my taste. I don't know if it's impeccable, but I've always, you know, since I was really young, I always was like focused on, okay,

my my sister and I each had her own room and I would pull, you know, magazine tear sheets of like, I want my room to look like this. And so I've always, you know, from a very young age, been very sort of hyper-focused on aesthetic, whether it's clothing or the way my room looks. I don't know why, but I've just always, I was born that way. So how does Tommy approach you when you guys start dating? You said that you guys became friends first. What was, is, does he have like a hip, pickup line? Does he hit on you a certain way? Well, it's interesting. His, I don't know that he had, his pickup line was probably, he said to me, you know, I should be with a girl like you. So I didn't really know how to take that. I was like, oh, okay. You know, Tommy at that time was running around.

He was, he was pretty wild in his day, I would say. And so I didn't really take that too seriously. Like I said, we were living on two different continents. And, you know, he would sort of invite me to things and then disinvite me to things. He was very scattered. He was all over the place. So I kept it like in the friend zone for a while until I really kind of knew and thought like, okay, he's really serious. Because I can't, you know, move. I've got two kids.

I'm not going to move continents, you know, for just, you know, dating. somebody or somebody that wants to, you know, somebody that wasn't serious. I wasn't going to uproot my whole life. When you guys did decide to get together, were you both aligned with designing things together? Or was that something that happened slowly over time? That's funny, because I remember the very first time Tommy showed me his house. I remember, like, just sighing, like having a big sigh of relief because I was like, oh my God, I like his house. That's a big one. I like his taste. I mean, I don't know if you've ever like, like, you know, dated somebody and like, you just can't go there because, you know, they have like

a horrendous pillow on their couch. You know, have Michael had black sheets when I first started dating. Black sheets were the wrong choice for many reasons. I was like, no. You fixed that. Yeah, immediately. So I understand that. So you didn't have to like get aligned with him on taste.

You guys both had an excellent taste. And when you met each other, you just expanded on that. It's funny. we used to play this game when we were dating and he used to open up a magazine and there used to be like, you know, a page where they show a few different items like say they'll show five different bags and he'll say, well, what's your favorite? And then I'd have to look and I'd pick and he'd say, yeah, that's my favorite too. So it was like, it was kind of funny this game. We usually picked the same thing. So I was like, oh, that's interesting. Our tastes are pretty aligned.

What was the first home that you guys decided to do together and how did that go because Michael and I need need some advice on this area. So the first project we worked on together was we bought an apartment at the Plaza Hotel, which I was like, wow, that's, I mean, I can't remember what year. It must have been 2008, maybe. At that time, it had only been a hotel, so it was really exciting. And we thought, like they just opened up the part of it for, yeah, okay. Exactly. And so that was the first thing we did together. And we kind of sat down and like thought, okay, what do we want to do? And we sort of wanted to make it feel like it was like from the old the Plaza Hotel.

So we had like, you know, these great Truman Capote obviously did his famous white ball at the Plaza. So we had like this great warhol of Truman Capote and we got black and white pictures of, you know, the white ball. we wanted to make it feel sort of classic and reminiscent of that time. You know, because when I walked into the space, I was like, wow, if these walls could talk. Because everybody from, you know, Maryland and the Beatles, it was, that was a very exciting project to do together. And so we kept it sort of classic and we did like, you know, reds and blacks. And I don't know. I think for us, we always start with where the house.

and what is the architectural style. I don't know. Where is this house that you guys are doing? No, we're redoing a house in Austin right now. In Austin. So, but you don't want to like end up with antlers on the wall. Right, you don't. Like,

your cowboy hats hung. Not that there's, well, I should I say, not that there's anything wrong with that. You can infuse it so it feels like you're in Austin without it being on the nose. Yeah. Yeah.

Yeah. I think it peppered in, like you want to have some kind of vibe where you are, I think. give it something like that, but, you know, it's always about the edit and the mix. How do you guys work when you work on a project? Because you guys have worked on so many projects, which everyone needs to check out your book, He'll Figure Homes. But how do you guys conceptualize each house? Like, what's the process? You mentioned that you first start with like sort of like, I wouldn't call it a theme. What did you call it? You said a...

Well, we kind of do mood boards. Mood board. We'll do like a little bit of a mood board where, you know, we, look for inspiration. So we, we look through other magazines and things and we take, it's, you know, the design process is very similar when you're designing clothes or anything else. It's like you'll look at something else for inspiration. You might see something and say, well, I like that from that, you know, that from that picture, but not in that color. And, you know, it's always about where you're getting your inspiration. And, you know, you can get inspiration from many different places. So we just we travel a lot. We get to see a lot of things. So do you pick the pieces out

from from everywhere and put it together? Like how does it all come alive? Yeah. I mean we we pick what we like. You know, it's like an editing process. Yeah. It's it it's interesting that you ask that because I don't feel like it's that different than designing a bag line or a clothing line or anything else. It's always about like a curation and an edit. What are some challenges that you've experienced along the way of your journey? Well, probably personal challenges. I mean, if I have to be honest, I think that, you know, my divorce was a huge thing in my life. It was a huge personal challenge that in one way I feel like it kind of set me back at least mentally like it did.

But I had to totally sort of reprogram everything after that. That was probably like there's sort of like my life before the divorce, my life after the divorce. Just the way you thought about relationships or life? Yes, about everything. And it was like I was probably, I'm trying to think how old I was. It was like maybe 38, 37, 38 around that age when I divorced. So, and I had two kids. And so that was like probably the biggest challenge in my life and the biggest traumatic thing that, you know, I had to.

start all over and figure out, you know, what to do with these kids and how not to traumatize them. What was I going to do? I'd stopped working. I mean, there was a lot. There was a lot going on for me at that time. It was a very difficult time. And then, you know, I didn't really know, was it going to stay in Monaco? I didn't know. I hadn't met Tommy then. I met Tommy three years later. But it was just like, how do I build, first of all, myself back up? And then, you know, how how do I take care of my kids and just how do I move forward from that? Because I'd only known being married, you know, to that man. And it was a very difficult time. In hindsight, outside of, like, in the marriage,

and you would obviously have not have changed the marriage. You've got two beautiful kids out of it. But are there things you would have done differently as a young person getting married or things that you would have set up differently looking back? Because when I'm hearing you talk, it's like, you know, your life was then in Monaco away from your family and then sounds like you stopped work. I just was wondering what the what the advice your younger self would be. You know, it's, that's a typical question for me to grapple with because I think, you know, I always sort of look at

things that that was my journey and maybe that was all meant to happen to get to where I am. So if I change that, I might not be here today. So I kind of view it like that. But I think, you know, I married young and I think that I, I think when I did marry, I didn't take a lot of things into consideration that maybe I should have. Like just, you know, I married somebody from a different culture. Maybe I was too young to get married. Maybe I wasn't ready to really get married. I don't know.

I mean, I question those things. You can always play the, what is it, the Monday morning quarterback. I don't know. I do try to learn from those things. I think, you know, obviously that wasn't the right. right decision for me. But then if I say that, then... No, no, I really relate to that perspective. And sometimes I have a hard time looking back. And my dad always says, you can't drive a car looking in the rearview. But I think there's

some people that have the perspective of, I did that and that's what got me in where I'm here. And then there's the others where sometimes like, hey, I shouldn't have done those things. And it's hard if you have, I think, your perspective or maybe even mine to kind of like go back because your life would not unfolded the way it is now. And I mean, honestly, when you think about it, okay, that marriage was a failure. But in my life, my failures have, you know, you only gain success from failure, right? I mean, you have several failures. And, you know, it's a failure in sense of the marriage, but it's not a failure in the sense of I have two amazing children from it.

And, you know, it's all water under the bridge. I was young, he was younger. It's passed. We're friends. We all have moved on. That's cool. You guys are friends. Yeah.

Now that you've had the successful marriage with Tommy, what do you think the secret or the tricks are to marriage? Or what is maybe your personal secret? I think, well, first of all, love, laughter is definitely one. I think, like, probably love laughter and respect. Those three things go a long way when it comes to marriage, I think. And you guys also work together, like Michael and I do, which I always say it's the most, challenging but rewarding thing. Like it's so rewarding to work together and it's so amazing to be able to work next to your spouse, but it is not without challenge. So how do you guys sort of balance

that? We work together in certain ways, but then we work together separately too. It's not like we're not together like working 24-7, which is nice. Which is nice. And he'll, what's interesting is He always asks me his opinion on things with Tommy Hilfiger. And I'll always ask him his opinion on things that I'm working on because I have, I'm creative director for Judith Lieber. I do a lot of other things. So we're both really, really busy. I think we both love working.

And so we both, you know, enjoy that. So it's not like I'm sitting there like, why are you working so hard? And he's saying, well, why are you going off there? That's helpful. I mean, we work together, but then we don't work together. I get it. I totally get what you're saying. You have your own projects going on.

How do you set up your day for success? What are your routines that you do? You know I'm going to ask you that. I knew that you were going to ask you that question. I was warned or told that I was going to get this question, and I was thinking about it. And I was like, you know, I obviously we travel around a lot. So the routine thing, I love routines. I mean, I would have to say my real routine is when I wake up.

I need a coffee. Like first thing. I mean, yes. What's your coffee order? The coffee is I have this fantastic machine. It's a Jura. J-U-R. Somebody bought it for me for a Christmas present.

And I was like, what is this machine? And it's a fabulous machine. And I put in the Lavatsa, crema, coffee beans, and it mixes it up. And it's a machine that you push. It can make anything, any kind of coffee. So I like my express.

so long. I have a couple of those and some water and that's like how I get my day going. And then, you know, Tommy and I, when we're home, we always drive together our son to school. So we both get in the car every morning and we drive Sebastian to school. And, you know, and then we come back and we both like to work out, try to get like a 45-minute workout in there with a trainer. What's your workout? Are you guys lifting? Pilates. So we're doing, yeah, we're lifting. We're doing more strength training. And I sometimes go to a Pilates with a couple of girlfriends in Palm Beach. And, you know, we are doing the best we can with that to try to keep it, you know, keep it all. Keep it all keeping it up. So many times during the day, I just want a drink

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We have not looked back since making the switch, and we feel better for it. So check them out. shop Branch Basics in 600 plus Target stores nationwide or Target.com. You can also use our code Skinny 15 to get 15% off at branchbasics.com slash skinny 15. Again, Skinny 15 for 15% off at branch basics.com slash skinny 15. One of my main concerns when it comes to my skincare is my under eyes. I take it very, very seriously. And what I notice is whenever I have to wake up really early with my kids, I'll have like puffy eyebags. And obviously, you guys know I use an ice roller under my eyes, but I also like a really nice eye cream. And the one that I've been using lately is by

Clarence. It's called Total Eye Lift. And so how I like to use it is I like to put a little bit on my index finger and then I like to pat it underneath my under eyes. And I go outward so I can also like pump the lymph a little bit. And I'll open up behind my ears. And I'll open up behind my ears and let the lymphatic drainage go to work with Claren's total eye lift cream. Okay, so this is what it looks like. It has a retinol-like technology, which is really, really cool. And everything about it is designed to help the eyes. It's like a four-in-one eye cream, if you will. So crow's feet, even like 11s between your eyes, which I sometimes get too, even the 11s between the eyes, which happen as you age. and of course, dark circles and for me, puffiness. I absolutely love pairing my facial manipulation

with their total eye lift. I think a mix of the two is so incredible to really depuff the under eyes. I've even gotten my husband into this because he sort of gets like a purple under eye situation. So if you're looking for plumber, smoother under eyes, I think this is a really great one to try. Like I said, just apply it gently underneath your eye, sort of going up. Sometimes I'll even apply it on the top of my eye. I really love this specific one by Claren's because 94 of the ingredients are of its natural origin, which I think is really, really cool. It's plant-based. It also boost collagen, which we love. Everyone loves boosting collagen after 30. I think that's an amazing benefit, which really firms the skin. And I think a hot tip when it comes to Claren's total eye lift is you

want to apply the eye lift before serum. This is really important. So they encourage always doing the eye cream first. So do it before your serum. I think it lays really nice under makeup, which is important to me as well. For me, at this point, it's all about prevention. I am so into preventative beauty. And I also like things to be non-invasive. I don't want to stick any needles underneath my eyes. So it's really nice to find an eye lift cream that works. This product is known to target every single wrinkle or any eye concern. around the eye. So it really sort of does everything. So I wanted to know what the order, like the exact order was. So this is the order that you want to use. Cleanser, toner, eye cream serum, thinest to thickest, and then a moisturizer. And then I like to use sunscreen after. And then if I'm doing makeup, I'll do makeup. What I'm really into is warming up the product before I use it. So I'll warm it up between my fingers. And then I'll just pat, pat, pat it under my under eyes, giving a little bit of lymphatic drainage. It lifts in 30 seconds. Like you can see it right away.

Clarence really does think of everything when it comes to preventative beauty. I have been a fan of this brand forever. My mom used to use it. And so it's really fun to be using this eye lift cream to prevent before it even happens. Don't wait until your 30s or 40s or 50s to use an anti-aging cream. This one is so important to your routine. Don't neglect your under eyes. You don't want them to be puffy. This is a great one to have in your arsenal. Also, it has hirungana extract in it, which is a plant retinol. This is as effective as retinol, but gentle on the skin. So if you want plumber, smoother, under eyes, check out Claren's total eye lift. If you're looking for something gentle on the skin, this is the new generation of the best-selling Clarence eye cream, the total eye lift.

This is available at Ulta, Sephora, and on Clarence.com. I get mine on Clarence.com. Like I said, pat, pat, pat under your eye every single morning before your serum. You will love this. If you want to be preventative, this one is amazing because wrinkles are reduced in 30 days. Retinal-like technology is in this product, which makes it really, really superior. And the fact to me that it boosts collagen is a no-brainer. If you want to firm your skin, plump your under eyes, and really kick your skincare up a notch.

This is such a beautiful product to use. To be preventative, I want to be very thoughtful about my under eyes. It's something that I want to really take care of. It's such a delicate, fragile place. And I want something that is really amazing with results, which is why I like this product so much. You guys have all seen Claren's everywhere. It's an iconic brand that everybody loves. I remember being inspired by this brand when I saw it on my mom's vanity when I was a little girl.

I feel like this is something that I'll even pass on to my daughter. I've noticed firmer skin and dark circles and puffiness reduced in like three weeks. So it works like a charm. You can go to clarence.com or Ulta or Sephora. What about your skincare routine? I'm sure you know I'm going to ask you this too. Do you have any specifics that you reach for for skin? I am, you know, I absolutely am obsessed with.

with the PV 50, the biologic. I need to get back on that. That's such a good one. I use it like twice a day. I'm obsessed with it. I just do what you tell me. Don't sleep on. Look at Michael's skin right now, Dee.

It's so shiny. It's like. But I will do what you tell me. No, your skin is looking great. I can see my reflection in it. Well, the lights are pretty good. No, but that that one is a good one. Your skin is really good too.

Thank you. I don't know. I should be asking you about your routine. I have some serious skincare tips. I love good skin. Well, you know, we've had so many people come on the show at doctors and experts and estheticians. And when they explain to me that the skin is the largest organ and that like, and you

start to, I think about it now the same way I think about, you know, taking care of other areas. But before, I was just like a dusty old saddle. Are you ready for what I just did? Because you have to hold on tight for this one. Okay. Okay. I had a baby two months ago.

I took my placenta and put it in a cooler. Then we took the cooler across the country. We had a doctor. To a doctor in Palm Beach. Oh. The doctor extracted exosomes out of my placenta. The audience is turning out now. That are one day old exosomes.

No, no. People do this. They get exosome therapy or stem cell therapy. Yeah, you've heard of. I'm sure you've heard of Xosomes. But they typically do it with other people's cells or other people's exosomes. So they take the placetone. exosomes and they put it, they package it up and then they bring it back to you and then

they put it in a needle and then they shoot the exosomes in your face and on your hair line. But the reason that it's because, so the reason this is a bit novel is most people do it that way, but because it was our shared placenta, it's her, she had the placenta, but it's I think it was her placenta. Yeah, you don't do anything for the placenta. It has half of my genes in it. So it's technically, we're going to claim the placenta. We can both, what I'm saying is we can both use that placenta.

for these kind of exosome procedures instead of getting it from like a stranger or another. It's different. So they injected it into your face? They injected it into my face. But she's the factory, if that makes sense, of the creation of the materials that usually get some else. But anyone can get their exosomes pulled and I'm not sure how. I'd have to ask the guy, but he was saying anyone can get them pulled and it's obviously like really good for your skin and your hair. And it was kind of a different one and I swear I noticed a difference.

Well, I think it's working. I think you both, have you shot these exosomes in your hair? I have not. Can you imagine when I do it's going to be? He wants to shoot them into Michael in a certain area. Oh, well, is that PG? It's not PG. We did a whole episode. Well, we left to.

Now this is really getting. It makes it grow. Spicy. Yeah, he doesn't say that. He said it in the episode. It says that it essentially gives you, like, if you are 40, maybe now you are, the cells are like, as if they were 30, right? So it, like, helps you.

Oh, my God. This podcast just took a left turn. You never know. Wow. Oh, my God. Okay. So it can grow. You know, we did almost have a walkoff the other day.

We almost had a walk off. We did almost have a walk off. No, I'm not going to walk up. This is fascinating. I love where it's going. It's continued. You never know. Okay. Back to entrepreneurship, because we do have a lot of questions from the audience about that.

What are some pivotal moments where you felt like you were really stepping into entrepreneurship, maybe with being the creative director of Judith Lieber, launching your own brand? Give us some details there. I kind of fell into it accidentally because. because I was advising Tommy, he was doing a preppy collection. And I, you know, I grew up in Rhode Island during this whole like the preppy handbook. And I said, oh, I had this bag. I was describing a bag to him that I had that you could, it had buttons and you could change the covers.

I was like, you know, this was the preppiest bag and you have to do this an adult version. And I was describing it very passionately. And he's like, well, you should do that. And so that's what got me started. And so when I started to do that, I was like, well, you know, I went and made a prototype, and I went to Mindy Grossman at HSN at the time and showed her this fabulous design. So that's really, you know, when I sort of started to get into the designing aspect of fashion. Like I said, I had been in the fashion business when I was really young.

I was modeling. I was modeling in Dallas when I was, you know, going to college. And then I did it a little bit in Paris. So I was like in that aspect in the fashion industry, but never on the design side. And what about what you're doing is creative directing? For Judith Lieber? Yes. So that came about because, you know, we were, we bought into the company Judith Lieber was sold

and it was sold to Jamie Salter at Authentic Brands Groups. They own several brands. And so that's a friend. And so we also bought into Judith Lieber. And Jamie just said, hey, Dee, why don't, you know, you're doing bags. Why don't you take over and be creative director? And I love the idea because I had known that brand for a long time. And when we first bought it, everybody was telling me that their, like, grandmother had a collection.

I kept hearing that. And I was like, okay, so we need to get the younger, you know, we have to introduce it to a younger audience and do, you know, more fun, quirkier kinds of bags with it. because it was a lot of like sort of floral and almost like decoey older lady designs. And so when I took over, that's when we started to do like French fries and the brick phone and things that were going viral and getting a lot of attention. So that was really exciting. You did add a lot of fresh air into the brand. When you say those things, I'm like, oh my God, I can remember where you see it.

It's really iconic. It's very smart. You're right. It did sort of have viral moments. Yeah, it was really, and that was really, you know, really a lot of fun. And, you know, I still do that. And that gives me a lot of joy. How do you think about real estate and where you guys decide to have homes? Is there a certain strategy that you guys adhere to? Oh, that's, that's an interesting question. I mean, I would like to pretend like there's a strategy. But there's really not. I think it's, you know, Tommy and I always say, it's like you just know it.

Yeah. It's kind of like meeting a, you know, a guy or something. Like you just kind of walk in that space or you see it and you just know. It's funny. When we bought our Connecticut house, we both walked in and the realtor was like, you know, talking this room, the square. Like we were both blocked out. We both looked at each other and like he pulled me into the room like where we entered

and he said, just tell her to hurry up and finish it so we could just buy this. Like he did not even care. And I was like, I know. I mean, we just, we walked in and we knew. And that's kind of like, it's more of a gut than it is a strategy. And I don't think that, I mean, that is our strategy. It's just a gut feeling. And it's never let us wrong.

Yeah. I mean, that's really it. You told me this off air, but I would love for you to tell the audience because I know it's in your book. What is your favorite home and why is it your favorite home out of all the you guys do? So my favorite home in the book is probably our Greenwich, Connecticut home. That was probably the second property that Tommy and I did together. And it's really kind of where we raised our son, Sebastian.

And that's the home that I just said when we walked in, it was like, hurry up and finish the tour so we can buy it. Like it was just, she didn't even need to, we were just like, walked in, we're like, we'll take it. What are the elements that you think makes? a home, a home. It's a combination of things. I think, you know, I think about this a lot because Tommy and I have obviously bought and sold and moved a lot, and it's hard to move. It's very disruptive, and it's stressful, right? But I think at the end of the day, what I've thought about is, it's like, first of all, it's wherever you are together. Okay? I mean, I could be in,

you know, it doesn't matter if I'm in a mansion or I'm in a tent. It's like where, where I'm with with my husband and my son is where I'm going to feel like I'm home. And, you know, it starts from there. So I think it's just, you know, it's filling a space with the people that you love and then things that you love and momentums and memories and places that you've gone. And, you know, you walk around and, and you see things, it's like your stuff, you know. Have you ever seen that George Carlin, he does a sketch where he's like, you know, why is it that, you know, you walk in and you never like anyone's home because it's their stuff, you know, you're only like your stuff. So you never feel at home. It's like you're surrounded by your things and your people

and, you know, you've created your own little haven in your nest and you feel safe. How long does it take you guys from start to finish to do the home the way you like to do it. Oh, it always. I mean, it never stops. It never stops. So you're constantly editing, constantly. And how do you decide, aside of maybe getting an incredible offer, when you're going to sell something? Like, when you're like, okay, we've, we've had this space and time to move on to the next. Or are there ones that you're like, we're never selling? Or is it always keeping it moving? You know, we kind of, we keep it moving. It's sort of like what other opportunities.

I mean, to be honest, I never really thought we were ever going to sell the Connecticut house. But I think COVID came and I think Tommy wanted to change. And, you know, we like to change things up. And then that's why we kind of sold Miami because then we were going to move to Pong. You know, we just like to switch it up. So there's no like, okay, this is the family home that we all grew up in. Nostalgia you're able to say, okay, it's time to onto the next. Yeah, we don't have.

I mean, we're actually in the process of selling a home that he's had for over 30 years, which is our Mustique home, which is sort of a big deal. I think it's a big deal for his kids because they've also grown up there. And I think that's why it's hard. There's so many memories that you leave behind, but, you know, ultimately you go forward and you're going to make new memories somewhere else. We saw you guys in Italy one time. You did. We almost went and said hi, but we didn't want to disturb you. It was at Los Scoglio.

We were across the restaurant from you guys, and we were kind of talking about the podcast, we didn't want to go up to you guys. But we saw that you guys were with Chris. What's the best advice that Chris Jenner's given you in business? I think she's just sort of fearless. Yeah. You know, she'll say things to me like, you know, oh, don't be stupid or don't be an idiot. Like, you know, she's just kind of fearless about going forward, and she's very bold.

And she does it in the nicest way with the biggest smile. but she's pretty fierce. And she's, you know, I think that they've called her like a velvet hammer. I mean, she comes off, you know, but she's a very savvy, shrewd businesswoman. So I think, you know, I've learned a lot from that. It's like you can still be shrewd and savvy and do it with a really big smile on your face and be nice. I had the, it was during our scheduling conflicts and I had some mics in my bag and thought it, but Lawrence, it would be inappropriate if I walked up to the table.

table and through the micstone so let's just do it here. He almost threw through the micstone in the middle of the table. And I'm like, no. I'm just, I'm just kidding. No. Just kidding. I would have never heard about it. When you decided to do your own brand, what did that look like?

How did you conceptualize that? You know, I think it ultimately, the concept would just be, you know, for things that, you know, it's my brand with my name on it. So I like to do things that I think, you know, women will feel. feel good in, we'll look good in, and it's like comes from my taste. I edited, I curated it. And it's just really as simple as that. It's just like what, you know, people that would think that I have good taste would trust me in producing something that would, you know, look good on them. And when you launch your collection, what are the favorite pieces that people are really drawn to?

You know, we do a lot of denim and we do a lot of like sort of cash. wear and things. Like the denim, there's a pair of jeans that just kind of slip on and comfortable. I travel a lot. So I like really comfortable, easy to wear clothes. Me too. So, I mean, it's not fussy. It's not super agreed. It's just like everyday easy to wear clothes. And they're not, they're very affordable. It's just, it's, you know, I'm not pretending to be, you know, Jean-Paul Gouchier or, you know, some, it's just they're just everyday, easy. to wear comfortable clothes. The striped sweater that you just gave me, everyone needs to go check out. It's so beautiful. Can you tell us what's called where they can find that sweater? I'm going to wear it over

my shoulders. The whole line, I'm in head to toe. This is all DO2. So the new fall line, we're on Northstrom online and we're also at some Macy's, selected Macy's stores. What you're wearing, you guys have to go watch YouTube is so cute. This is all designed by you. It's cute. This is all D.O. And even the shoes, These are old shoes. I'm not doing shoes anymore, but the shoes are Dio, you know, the sweater. It's just kind of sort of casual wear, but it's put together. And we've done, like, what's kind of fun is we've done pieces that are very interchangeable. So it's, like, easy to sort of mix and match.

You don't need to think about, oh, what top is going to go with these pants. And, you know, some women are not as at ease with putting together separates as, you know, some women can do it. some women can't. I also think, too, it's sort of like a time saver. Yeah. You know, that's the way, it's nice to have it just ready to go to grab. Yeah. It's like you remember granitals with the kids and think they could. It's kind of like, you know, easy to put together. When you put together an outfit yourself, what are your styling points? Because like I said earlier, you do have a great perspective and point of view on that. A, it's comfort. And, you know, I would say that my style is more sort of classic and I lean towards more sort of classic and feminine and sort of timeless. So you're not

going to find like super trendy or I'm not trying to be like super sexy and like showing. You know, it's just kind of easy classic feminine. You know who has a really big point of view on style. Oh. Yeah. Well, I'd love to hear it. No, but I don't think it's. that. Just you sitting all quiet. I'm not. I just think that I just, well, my perspective is it like it, it literally, it should never look like you tried so hard.

Yeah. Like it should just be effortlessly classic always, I think. Yeah. I agree with that. The other day I got a rash on my chin. And one of the things I did was I immediately ran to take my probiotics. So I up to my dose because whenever I have any kind of rash or any kind of pimples. I feel like it's my gut telling me something. The probiotics that I take are by Just

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You know what I'm really into? A red light face mask. Okay. How I use it is every morning I wake up before my kids and I put a red light face mask on while I meditate. It's such a good habit stack. It's so easy and it tells my brain it's time to wake up. I have been doing this for the last year, this habit stack and it's worked really great. The one that I've been using is by Bond Charge. Bon Charge is a holistic wellness brand with a huge range of evidence-based products to offer. optimize your life in every way. What I like about this brand is it's founded on science, but it's inspired by nature. So if you're looking for premium wellness products to help you sleep better, perform better, have energy, recover faster, balance hormones, they really have you covered.

They have these blue light glasses that are amazing for nights. I love them when I'm winding down and reading my Kindle on dark mode. They also have an infrared sauna to the red light therapy, which is what I love, their red light face mask. They also have some EMF, management things on their site that are really great. You kind of can't go wrong. If you're looking for something that helps with wrinkles, fine lines, sore jaw, migraines, acne, scar tissue, or if you're like me and you just get like a little rash sometimes around your mouth, the red light therapy is really awesome for that. It's currently the bond charge holiday sale so you can save a massive 25% off. Just head to bondcharge.com and your 25% off code will be automatically added to your order. The sale will end on the

31st of December 2025, so hurry and don't miss the massive chance to save big on your favorite bond charge products. Quick break to talk about Square. We love Square. You should love Square. And that's because it makes checking out of stores and vendors so much easier. And it gives the power for anyone that wants to stand up a simple store or checkout process, the ability to do so. What's amazing is I don't have to travel with a bunch of cash to go and do the checkout process. What's amazing about it, one of the first things I notice is how easy it is to use and how easy it is to checkout. And how easy it is to checkout. What I love about it is how flexible Square is. I've seen it works seamlessly for all kinds of businesses and even small vendors. So if you've been building a business or thinking about building

a side hustle and you've been doing that in person, you can now also take it online because with Square you can expand online and Square makes it simple to set up a store in just a few minutes. It's perfect for those wanting to expand beyond brick and mortar. And like I said, it makes the user and the customer experience so seamless and easy. Square supports all major credit cards and payment methods, including your contactless options like Apple Pay and Google Pay. Check out if you fast and easy for your customers. So whether you're just getting started or looking to grow, it gives you the tools to do both without making things more complicated than they need to be, which so many people and so many companies do. So check them out. Square keeps up so you don't have to

slow down. Get everything you need to run and grow your business without any long-term commitments. And why wait, right now you can get up to $200 off square hardware at square.com slash go slash skinny. That's S-Q-U-A-R-E dot com slash go slash skinny. Run your business smarter with Square. Get started today. This episode is brought to you by The Skinny Confidential. I created a candle for myself, actually. I wanted to create exactly what I wanted in a perfect candle. So as the story goes, when Zaza was born, I lit all my favorite, very well-known candles. You guys all know these brands, and I noticed that my brand new baby was coughing so deeply. I couldn't figure out what it was, but something told me that there was something in the candle.

And so I talked to a lot of holistic doctors, and they said that a lot of the wicks in candles have something really toxic in them. And it comes out in the air when you light the candle. So I got rid of all my candles and I started fresh with beeswax candles. And while I was buying all these beeswax candles, I realized there was a gap in the market because they weren't pretty. So I set out to create my own clean, non-toxic candle for a better home. I just feel like this is a better choice because this candle has three ingredients and it's scented

with eucalyptus oil, which is organic. And the wick is an all natural cotton wick. So the Skinny Confidential team and I really thought of everything for you to make a better choice for the home. I got rid of all the candles in my house and this is one of the only candles that I use. If you want to grab our non-toxic candle for 20% off, just go to shop Skinnyconfidential.com and you'll automatically get the discount. It's 20% off at shopskinneyconfidential.com to November 1st. When I first got together with him, he had to help me edit my wardrobe. This is, by the way, like, wow, I'd throw away there. 10 years ago, 10 years ago, you had to come in and we had to do a lot of donating. Oh my God, that's like a Kanye thing. Well, I've said that. It actually was exactly

that. I've said that on the show, and I don't know if you should say that anymore. When I was 21, this is a long time ago, but he definitely had to help me edit it. And you do have to, have a very specific point of view on style. No, but it's not like a, I just, I just think that it should, I just like to clap. What's the biggest turnoff for you when you see like a girl walking? I want to know what they're like, you just crack this. You see a girl wearing something like, and you're like, oh my God. I banned sweatsuits in the office.

I walked in and all the girls were in sweatsuits. I said, that's not what we're doing here. No. I don't know if that was offensive. But I was like, listen, like, I'm not coming into a space that's supposed to be presentable and have people lounging around and they're like homework. Suits? No, I don't like sweatsuits. I don't mind a sweatshirt or a sweat pant, but then I think you have to dress it up with a top. Like, I say either, like, I don't like baggy, baggy. He says, this is what he says. He doesn't like baggy, baggy. Like, you know what I mean? I might be in baggy baggy right now, but I have to lose 30 pounds after a baby, so you're not going to get me in tight. No, no, that's different. But, you know, like when I think, I think it should just look like someone has put some effort into it. Like, they care. Because I think it's a reflect, like if you, it shows that you care about. not, well, a lot of things, right?

Yeah. And so the things that are turnoffs to me is when it's like, I just rolled out like this. I'm like, no, let's not do a rollout, you know? His mother is a half Japanese, so she has, she's very specific with how she puts her looks together. So I can see why. Yeah, well, you can't, most people don't think like,

hey, that's a Japanese guy when you look, but my grandma was full Japanese. Wow. And she was very, like, she was very opinionated. That's fascinating. Oh, no. Well, Japanese have, we were talking about this earlier. With Miles, I love that Japanese style.

I was in Tokyo. But they like baggy. Yes. They like baggy. But not like sloppy baggy. I have to be careful because, listen, I work with a lot of women, but I guess I'll just say I don't like when people look sloppy, men or women. Does Tommy ever get in a pair of sweatpants and relaxers? He's always dressed up.

There's no problem with getting sweatpants and relaxing, just not in... I mean, when we travel, okay? When we travel, maybe we like to be comfortable. That would be like the time where we're... in sweatpants, but I also prefer Tommy to be, you know, sometimes he throws on his hat. I'm like, you don't really need that baseball hat. Tommy, come on. Like, you're, you know, you're an older, sophisticated, like, you know, you're a fashion designer. Let's get, let's keep it, you know, not so casual. There's a whole manipulation. You just tell them that you say hats equal hair

loss. Ah. I don't think that's true. Yeah, that's true. Chat, GPT. I also think that as men, I'll beat up the men for a little bit, as they get older, should lean more into like the handsome classic look yeah like when you see a guy and it's like we're holding on to also women by the way okay well i didn't want to say it but that adhered i i would say i can say that maybe because i'm a like there was things i could get away with when i was younger that maybe i can't get away with now and i just think you just got to recognize that a little bit i yeah i think so you have to tell us about your amazon prime video docu-series that helps female entrepreneurs which is amazing oh my god i'm so excited about this show. So it is with Serena Williams. Cool. That's cool. Winnie Harlow. It's with Hannah

Bromfman, Isabella Grutman, Lauren Ridinger. Oh my gosh. I didn't realize this was this show. Yeah. Do you know the show? No, they came and talked about it. Keep going. Keep going. Yeah. I didn't realize that. And my girlfriend, Telia Motola, Telia, Tilia, Tali, who's, you know, a superstar, Latino superstar. And it's really interesting. When I first told people, that I was doing the show, I think they automatically go to like a housewives kind of thing, but it's not that at all. It's really sort of like a behind the scenes look at all of our lives. We all work in some capacity. We all have different sort of storylines. Like Lauren's storyline is obviously she's running this huge company, Market America, and she just has been recently widowed

and her struggles with that. And, you know, my story is my story where, you know, I'm, you know, starting businesses later in life and follows that. And Isabella is just starting out her jewelry line and she's got young kids and we're, you know, all friends and we're all trying to support one another. But and then, you know, Serena has her thing. So it just sort of follows us behind the scenes to show, you know, how we're doing things. And it's really, you know, it's hopefully to inspire women, you know, who are, who are thinking about maybe starting a business. this or wondering, you know, how we do this or what to do. It's more trying to inspire and teach women. It's not like we're not throwing drinks at each other at like a day drinking and getting

in fights. I think that's great. I love, love, love the female entrepreneur aspect. Yeah, it's called CEO Club. CEO Club. CEO Club. Love it. Can you leave our audience with one piece of advice for female entrepreneurs? I think stay fierce. And I think that, you know, if you, if you lead with passion and compassion and stay true to, you know, what you're trying to set out to do and that you feel is a right thing to do, then, you know, you'll, you'll ultimately be successful. And, you know, one of my favorite expressions is if, and this actually comes from Christian or two, is if somebody says no, you're asking the wrong person. Agreed. Dad used to say, talk to the head,

not to the feet. I'm going to apply that to you, too. If you say no, I'm asking the wrong person. As it relates to our relationship, who else is there to ask? You never know.

I don't have the ability to say no in our, it's kind of like a no and then we'll circle back. Well, you have kids. You're going to be outnumbered soon, right? We have three now. Oh, you have three. Yeah.

Wow. They're here in the city with us. We're hanging on by a thread. Oh my gosh. Are you done? is that we don't know oh i don't know i can't decide how many do you have you have three well we have seven combined i know seven combined i highly do not recommend that that's a lot that's like you seven seems a little excessive no it's it is fun it's like a whack-a-mole game it's like you know you've

got one thing settled and then another pops up it's just like you know things it's not boring no it's never boring so if you like whack-a-mole then i go for it hey so what is the right number then if it's not seven. I'm going to get trouble answering that question. She has to say seven. Seven's the right number. She thinks it's seven. Is it more than three or is it like, hey, three is good? I'll just like wink

if you catch my drift. I think three is good. Yeah, I get worried because right now, well, there's like more physical challenges because they're so young and you need to help them with everything and like get them dressed and pick them up. But I'm- One of them decided to take their shoes off in Central Park the other day and run around.

Yeah. Yeah. I will just say, because I'm a lot older than you guys and my kids are, you know, in their 30s now, I would say that I think when kids are young, like you guys have them, it's one thing and it's like really fun. And it's tiring, but it becomes a whole different kind of responsibility when they get a little bit older. That's what I think about. You're going to have your hands full. At the same time, quickly. Just don't get too over ambitious with that.

Is that a terrible thing to say? No, it's honest. But everyone that's a parent that talks to us that has children that are older or have gone through adolescents or teenagers say, like, well, when they become that, it's going to be a lot. And so I think, like, if you have, ours are five, three newborn. So it's going to come like in a big wave fast all of a sudden, right? Be prepared.

It's just at any age. It's a huge responsibility being a pastor. It changes everything. You guys know that. So, I mean, I can't tell people how many kids to have because I don't know what their threshold. Yeah. You know, what their patience and tolerance threshold is. Mine is, you know, as I've gotten older, it's gotten much less. So, you know, but like I said, we're good. Seven. I won't even have pets because I'm like my, my responsibility threshold is my cup runneth over with responsibility right now. Well, and before you leave, I need to get that old girl's Quaker school recommendation. guys. The Quaker girl, yes. We have a giveaway going on. Can we give away like your favorite pieces in the collection to one audience member? Absolutely.

Yes, I'd love to do that. Okay. All you guys have to do to win the giveaway is one personal win. You just need to follow your line, which you can tell us what the Instagram handle is. It is at Dioclepo. Okay, perfect. Follow that Instagram handle. And then tell us your favorite part of that.

this episode on my latest post at Lauren Bostic. One of you will win Dee's favorite picks from her collection. Definitely go check out her book. It's so beautiful. He'll figure homes and go watch your show on Amazon Prime too. When is it out? It is out, I believe, the early part of 2000 next year. Okay. Okay. What a great group of women too. Right? Yeah. So lucky. It's going to be awesome. I'm really excited about it. Dee, thank you for making this happen. We're so grateful. come back anytime. Thank you. Well, hopefully it won't take three years to come back. No, no, no, no. It was worth the buildup, I think. And by the way, next time you see me in Italy, come over. Oh, we will. No, no, no, no, now we will. That's my favorite restaurant.

We don't want to bother. We don't want to bother. You know, it would have been highly inappropriate at that time. Oh, I don't think so. We were also with some unruly characters that are in our friend group. There was a lot of rosé. There's a lot going on. But next time would have been fun. Yeah, we'll come say hi next time. Next time for sure. And I'll probably have the mics. Thanks, Dee. Thanks, guys.