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

Oct 30, 2025

Dee Ocleppo Hilfiger, former model and visionary designer, shares her journey from Wall Street to fashion, emphasizing her creative role with Judith Lieber. She discusses the balance of family life with her husband, Tommy Hilfiger, and offers secrets to a lasting marriage. Dee outlines her brand, DO by Dee Ocleppo, emphasizing comfort and style. She reflects on parenting bilingual children in Monaco and shares business insights inspired by Kris Jenner, aiming to empower female entrepreneurs. Don't miss her skincare tips and favorite home design stories!

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ADVICE

Edit Ruthlessly Like A Designer

Treat designing homes like designing clothes: curate and edit relentlessly.
Choose pieces by strong curation rather than matching everything perfectly.

INSIGHT

Three Pillars Of A Lasting Marriage

Dee summarizes marriage essentials as love, laughter, and respect.
She credits these three as foundational to a thriving long-term relationship.

ANECDOTE

Work Together, But Also Separately

Dee explains she and Tommy work together but also maintain separate projects to avoid 24/7 overlap.
They consult each other for opinions while preserving individual creative spaces.

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#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

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This episode is sponsored by SYNERGY

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This episode is sponsored by Branch Basics

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