The Skinny Confidential Him & Her Show 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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Meeting Tommy Changed Her Path
- Dee recounts meeting Tommy in the south of France after living in Monaco post-divorce with two sons.
- She describes moving continents and how that relationship changed her life's trajectory.
Rebuilding After Divorce
- Dee shares she divorced in 2003 and was a single mom to two sons before meeting Tommy three years later.
- She explains that rebuilding after divorce was a major personal challenge.
Shared Taste Fuels Collaboration
- Dee and Tommy discovered shared taste by playing a magazine game and often picked the same items.
- She uses this alignment as a foundation for collaborating on design projects.
