Podcast Summary: The Skinny Confidential Him & Her Show

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

Released: October 30, 2025
Hosts: Lauryn Evarts Bosstick & Michael Bosstick
Guest: Dee Ocleppo Hilfiger (designer, entrepreneur, philanthropist)

Overview

In this lively and candid episode, Lauryn and Michael Bosstick sit down with Dee Ocleppo Hilfiger. Dee is known for her sophistication, entrepreneurial spirit, and as the creative powerhouse behind her lifestyle and fashion ventures, including D O by D and her role as Creative Director at Judith Leiber. The conversation dives into Dee's international life journey, blending families, her design philosophy, approaches to a lasting marriage with Tommy Hilfiger, and empowering women in business—while always keeping things tangible, relatable, and humorous.

Major Discussion Points & Key Insights

1. Dee's Personal Journey & Early Life

• Roots and Upbringing ([01:44]):

  • Grew up in East Greenwich, Rhode Island, with immigrant parents—her father from Turkey, mother from England/Canada.
  • Describes a strict upbringing:

    "My dad was super strict...could never go to boy-girl parties. Couldn't do basically anything that all my friends were doing." — Dee Hilfiger [04:44]

• Early Independence and Exploration ([05:03]):

  • Attended an all-girls Quaker school; felt restless and looked for freedom, which she found moving to Dallas.

• Multiple Careers Before Fashion ([02:49]):

  • Modeled in Paris, worked on Wall Street as a commodities assistant trader; describes having "ten lives, not even nine."

2. Life in Monaco, Marriage, & Meeting Tommy

• Living Abroad ([03:22]):

  • Lived in Monaco while married to Italian tennis pro; raised multilingual children.
  • Despite the glamour, it was "kind of like living anywhere," with normal mom routines.

• Meeting & Marrying Tommy Hilfiger ([06:08]):

  • Relationship started as friends on different continents; Dee was cautious about uprooting her life:

    "I wasn’t going to uproot my whole life...for just, you know, dating somebody or somebody that wasn’t serious." — Dee Hilfiger [06:20]

3. Collaborative Design & Family Life

• Shared Aesthetic ([07:31], [08:15]):

  • Immediate relief at liking Tommy's taste in design.
  • Played games picking favorite items in magazines—almost always matched in choices.

• First Home Together: The Plaza Hotel Project ([08:50]):

  • Made their shared apartment at The Plaza feel classic and inspired by the building’s legacy (Truman Capote, Warhol art).
  • Emphasis on starting with mood boards and "editing and mixing" for each home.

• Design Process is Like Fashion ([11:51], [12:09]):

  • "It's always about, like, a curation and an edit." — Dee Hilfiger

4. Overcoming Personal Struggles

• Divorce and Reinvention ([12:15]):

  • Divorce in her late 30s was a defining challenge—forced to "totally reprogram everything" and rebuild for her kids.

• Lessons from the Past ([14:10]):

  • No regrets:

    "That was my journey...if I change that, I might not be here today." — Dee Hilfiger [14:10]

  • Sees failure as the route to personal growth.

5. Secrets and Realities of a Strong Marriage

• Keys to Relationship Success ([16:16]):

  • "Love, laughter, and respect. Those three things go a long way." — Dee Hilfiger

• Working with a Spouse ([16:48]):

  • Balance is in working together on some projects, separately on others; shared understanding of ambition.

6. Daily Routines, Wellness, Skincare, and Parenting

• Morning Rituals & Family Time ([17:45]):

  • Starts day with Jura coffee machine, drives son to school with Tommy, tries to fit in strength training or Pilates.

• Skincare Favorites ([29:04]):

  • Adores Biologique Recherche’s P50 lotion; twice-daily regime.
  • Discussion of innovative (and unusual) skincare, like exosome/placenta treatments.

• Parenting Real Talk ([57:11]):

  • Dee and Tommy have seven combined children ("highly do not recommend that... it’s like whack-a-mole" [57:19]).
  • Honest notes about the evolving nature of parental responsibility as kids grow up ([58:14]).

7. Career as a Fashion and Lifestyle Entrepreneur

• Venturing into Bag Design & Judith Leiber ([32:32], [33:43]):

  • Inspired by a childhood "preppy" bag—Tommy’s encouragement led her to prototype, then full accessory lines.
  • As Judith Leiber Creative Director, revamped the brand:

    "We started to do, like, French fries and the brick phone...going viral and getting a lot of attention." — Dee Hilfiger [34:48]

• Launching D O by D: Design Ethos ([41:02]):

  • Focus on comfort, timelessness, everyday wear: "Easy, classic, feminine."
  • Styles meant to be interchangeable, affordable, and accessible ([42:46]).

8. Home, Real Estate, and Style Philosophy

• Homebuying Approach ([35:18]):

  • "You just know," relying on gut more than strategy.

• Home as a Feeling ([37:00]):

  • "Where I’m with my husband and my son is where I’m going to feel like I’m home."
  • "It’s filling a space with people you love, and then things you love and memories."

9. Advice from Industry Icons & Pay-It-Forward

• Business Wisdom from Kris Jenner ([39:59], [56:44]):

  • "She’s kind of fearless...a velvet hammer...you can be shrewd and savvy with a big smile."
  • "If somebody says no, you’re asking the wrong person." — (Kris Jenner as quoted by Dee Hilfiger)

• Tips for Women Entrepreneurs ([56:08]):

  • "Stay fierce...lead with passion and compassion and stay true to what you’re trying to set out to do."
  • Emphasizes resilience and authenticity.

10. Upcoming: Empowering Women through Media

• New Docuseries: CEO Club ([54:04]):
  • Co-starring with Serena Williams, Winnie Harlow, Hannah Bronfman, and more.
  • Not a reality show; meant to inspire, show real entrepreneurial journeys.

Notable Quotes & Memorable Moments

• On failure and growth:

  "You only gain success from failure...it’s a failure in sense of the marriage, but it’s not a failure in the sense of I have two amazing children." — Dee Hilfiger [15:32]

• On personal style:

  "My style is more sort of classic and I lean towards...timeless. So you’re not gonna find super trendy or super sexy—just easy, classic, feminine." — Dee Hilfiger [43:41]

• On family chaos:

  "It's like a whack-a-mole game...never boring." — Dee Hilfiger [57:26]

Timestamps for Key Segments

• [01:34] Dee’s Multi-Faceted Life Pre-Tommy (modeling, Wall Street, Monaco)
• [07:31] Aligning Tastes: The Magazine Game
• [08:50] Designing Their First Home at The Plaza
• [12:15] Divorce and Reinvention
• [16:16] Secrets to a Thriving Marriage
• [17:45] Morning Routines & Wellness Habits
• [29:04] Favorite Skincare Products & Wild Treatments
• [32:32] Entering the Bag & Fashion Business
• [33:43] Revamping Judith Leiber—From Grandma’s Closet to Viral Hits
• [35:18] Homebuying Philosophy: It's All Gut
• [37:00] What Makes a House a Home
• [39:59] Kris Jenner’s Fearless Business Advice
• [41:02] Starting D O by D: Brand Vision
• [54:04] Launching "CEO Club" on Amazon Prime
• [56:08] Closing Advice for Female Entrepreneurs

Tone and Style

The conversation is candid, supportive, and full of practical wisdom, with humor and warmth throughout. Dee is earnest, honest about challenges, and passionate about design, family, and empowering others. Lauryn and Michael keep the mood lively and relatable, mixing personal anecdotes with tactical insights.

For Listeners

For those seeking inspiration on navigating blended families, entrepreneurship, creativity, building enduring relationships, or simply living beautifully and authentically, this episode delivers a rich blend of personal storytelling and actionable advice. Listeners also get a sneak peek into the glamorous, yet grounded, world of Dee Ocleppo Hilfiger, punctuated by wisdom from icons like Tommy Hilfiger and Kris Jenner.

Dee Ocleppo Hilfiger

Instagram: @IOCleppo
Products: D O by D (Nordstrom, Macy’s), Judith Leiber handbags, “Hilfiger Homes” book
Upcoming: CEO Club on Amazon Prime (early 2026)

(For further context and to enter the episode’s giveaway, see @LaurenBostick’s Instagram.)