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

The Skinny Confidential Him And Her Show

Dear Media

Education, Business

4.5 • 14.5K Ratings

🗓️ 30 October 2025

⏱️ 61 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

#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.

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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

Transcript

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0:00.0	The following podcast is a Dear Media production.
0:04.7	She's a lifestyle blogger extraordinaire.
0:07.5	Fantastic.
0:08.5	And he's a serial entrepreneur.
0:10.8	A very smart cookie.
0:12.2	And now Lauren Everts and Michael Bostic are bringing you along for the ride.
0:16.3	Get ready for some major realness.
0:18.1	Welcome to the skinny confidential, him and her. Today we're sitting down
0:26.1	with someone who I really admire that I really enjoyed talking with, and that is Dee Hilfiger.
0:32.2	She's a former model, a visionary designer, entrepreneur, and philanthropist. She is married to the one and the only
0:39.7	Tommy Hilfiger, and she's known for her effortlessly sophisticated style, which you guys have to watch
0:45.5	the YouTube because she's wearing the cutest outfit from her own brand, D.O. By D. In this
0:52.3	episode, you'll get an exclusive look at how she thinks about designing her iconic
0:56.3	Hilfiger homes, her secrets to a thriving marriage, and how she collaborates with Tommy
1:01.6	on designing The Vision.
1:03.6	And you should also know that she is a busy mom.
1:06.5	She has seven kids.
1:07.7	She really does it all.
1:09.3	D. Hilfiger, welcome to the Him and Her show.
1:12.4	This is the skinny confidential, him and her. So happy we made this happen.
1:18.7	Yes, finally. It's been three years in the making. Yes, it has. First question dive in. I think
1:23.3	people look at your life and they think, wow, so lucky, so easy, but it wasn't always like this for you.
	...

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