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

30:59So it's technically... Oh, I'm 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. 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 somewhere 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.

31:28And it was kind of a different one. And I swear I noticed the difference. Well, I think it's working. I think you both, have you shot these exosomes in your face yet? 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 or should I talk for that? We did a whole episode on this. Well, we have to. Now this is really getting spicy. 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.

32:00Oh, my God. This podcast just took a left turn. You never know. Wow. Oh, my God. OK. So it can grow. You know, we did almost have a walk off the other day. We almost had a walk off. We did almost have a walk off. No, I'm not going to walk off. This is fascinating. I love where it's going. Let's continue. You never know. OK, 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?

32:29Give us some some details there. I kind of fell into it accidentally 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 in 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.

33:13So 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 as 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.

33:56They own several brands. And so that's a friend. And so we also bought into Judith Lieber and Jamie just said, Hey D, 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 this 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 deco-y 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 you know going viral and getting a lot of attention.

34:47So 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. You 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 an interesting question. I mean, I would like to pretend like there's a strategy, but there's really not.

35:26I think it's, you know, Tommy and I always say it's like you just know it. It's kind of like meeting 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 talking this room the square foot 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 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.

36:13It's just a gut feeling and it's never led 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 homes 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.

36:51Like 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 make 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 walk in and you never like anyone's home because it's their stuff.

38:12You only like your stuff. So you never feel at home. It's like you're surrounded by your things and your people and 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, always. I mean, it never stops. It never stops. So you're constantly editing. Constantly. And how do you decide, outside of maybe getting an incredible offer, when you're going to sell something? Like when you're like, okay, we've had this space and time to move on to the next. And are there ones that you're like, we're never selling?

38:47Or 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 Palm 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 on to 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 Moustique home, which is sort of a big deal.

39:28I 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 ultimately you go forward and you're going to make new memories somewhere else. We saw you guys in Italy one time. We almost went and said hi, but we didn't want to disturb you. It was at Los Coaglios. We were across the restaurant from you guys and we were kind of talking about the podcast and 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 Kris Jenner's given you for in business I think she's just sort of fearless yeah you know she you know she'll say things to me like you know oh don't be 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 I think that they've called her like a velvet hammer.

40:24I 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 and threw the mic stone. So let's just do it here. He almost threw the mic down in the middle of the table. I'm like, no. I'm just kidding. Just kidding. I would have never done that. When you decided to do your own brand, what did that look like?

41:00How 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 good in, will look good in. And it's like comes from my taste. I edited, I curated it. And it's that's 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?

41:45You know, we do a lot of denim and we do a lot of like sort of casual 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 Gaultier 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.

42:24It's so beautiful. Can you tell us what's that, 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 Nordstrom 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. This is cute. This is all Dio. 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.

43:03so 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 I it's nice to have it just ready to go to grab yeah it's like grant You remember granules with the kids and 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.

43:41A, 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 part 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 great You sitting all quiet over there. I'm not. I just think that. I just, well, my perspective is it should never look like you tried so hard. Yeah. Like it should just be effortlessly classic always, I think.

44:30Yeah. 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 upped 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 Thrive. I have been taking this specific brand forever. I have had the founder on the podcast three times because she's so knowledgeable about the gut. And the products that she has have so much integrity behind them. They're award-winning verified products and everything is designed to help with your digestive health and your full body wellness So that's why whenever I get any kind of flare-up whether it's a pimple or like I said a rash I reach for my just thrive probiotics You really can't go wrong.

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46:07And just so you know, I like to take this in the morning with my lemon electrolyte water. I do usually like two or three. That's justthrivehealth.com code TSC. 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. Bond Charge is a holistic wellness brand with a huge range of evidence-based products to optimize your life in every way.

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49:01And 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.

49:46And 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.

50:24So 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 shopskinnyconfidential.com and you'll automatically get the discount. It's 20 % off at shopskinnyconfidential.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, 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.

51:02It actually was exactly I've said that on the show and I don't know if you can 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 a very specific point of view on style. No, but it's not like a, I just, I just think that it should. What's the biggest turnoff for you when you see like a girl walking? I want to know what that like, do 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.

51:42You don't like sweatsuits? No, I don't like sweatsuits. I don't mind a sweatshirt or a sweatpants, but then I think you have to dress it up with a top. Like I say either, I don't like baggy baggy. 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. 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 a lot of things right yeah and so the the things that are turn offs to me is when it's like i just rolled out like this no let's not do a rollout 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 and she was very like she was very opinionated fascinating oh no japanese have incredible we were talking about this earlier with miles that they 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 does tommy ever get in a pair of sweatpants and relax or is he always dressed up there's no problem with getting sweatpants 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 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 oh i also know just tell them that you say hats equal hair loss ah i don't think that's true that's true chat 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 adhere i i would I can say that maybe because I'm a woman.

53:54Like there was things I could get away with when I was younger that maybe I can't get away with now. And I think you just got to recognize that a little bit. Yeah, I think so. You have to tell us about your Amazon Prime Video docuseries 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 Bronfman. Isabella Grutman. Lauren Reitinger. 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. Yeah I didn't realize that.

54:31And my girlfriend Talia Mottola Talia Soti 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.

55:15And Isabella is just starting out her jewelry line and she's got young kids and 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 it's hopefully to inspire women you know who are who are thinking about maybe starting a business 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.

55:53I think that's great. It's not that kind of show. 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 like passion and compassion and stay true to, you know, what you've, what you're trying to set out to do and that you feel is the 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 and this actually comes from christian or two is if somebody says no you're you're asking the wrong person agreed my dad used to say talk to the head not to the feet i'm gonna apply that to you too if you say no i'm asking the wrong person who else as it relates to our relationship who else is there to ask you never know i'll find someone 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.

57:02You'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. What's the right number? You have three? Well, we have seven combined. Seven combined. I highly do not recommend that. That's a lot. That's like, you know... Seven seems a little excessive. That's fun though. 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 are popping up.

57:35No, 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 in 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's good? I'm just like, wink if you catch my drift. I think three is good.

58:00yeah i get worried because right now well there's 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 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 you're gonna have your hands full at the same time like quickly get too over ambitious with that is that a terrible thing is a parent.

58:47No, it's honest. No, but everyone that's a parent that talks to us that has children that are older or have gone through adolescence 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 newborns, 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 parent. 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, you know, what their patience and tolerance threshold is.

59:22Mine 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 all girls Quaker school recommendation because the quaker girl yes we have a giveaway going on it 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 this episode on my latest post at lauren bostic one of you will win d's favorite picks from her collection definitely go check out her book it's so beautiful hillfiger homes and go watch your show on amazon prime too when is it out it is out i believe that the early part of 2000 next year okay 2026 what a great group of women too right yeah so lucky really it's gonna be awesome i'm really excited about it d thank Thank you for making this happen.

1:00:38We're so grateful. Come back anytime. Thank you. Well, hopefully it won't take three years to come back. 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. Now we will. No, no, no. Now we will. That's my favorite restaurant. One of my favorite restaurants in the whole world. 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. There was a lot of rosé. There was a lot going on. but next time that would have been fun yeah we'll come say hi next time next time for sure and I'll probably have the mics thank you thanks guys