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October 30, 2025 61 mins

#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 +1 (512) 537-7194.

 

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

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