If Jewels Could Talk with Carol Woolton

Episode: JENNIFER TILLY: HOLLYWOOD'S QUEEN OF JEWELS

Date: December 11, 2025
Host: Carol Woolton
Guest: Jennifer Tilly

Episode Overview

This episode explores the sparkling world of Jennifer Tilly, acclaimed actress, poker champion, and legendary jewelry collector. Host Carol Woolton and Jennifer dive into the stories, passions, and inspirations behind Jennifer's remarkable jewelry collection—ranging from legendary designer pieces to Hollywood memorabilia. The conversation is rich with personal anecdotes, historical insights, and practical advice for jewelry lovers and collectors.

Key Discussion Points and Insights

Jennifer’s Jewelry Collecting Journey

• Two Professional Hobbies
  • Poker (Women’s Poker Hall of Fame inductee) and collecting jewelry (02:20).
• Early Influences and Beginnings
  • Started with Miriam Haskell and Chanel costume jewelry in the 1980s (11:59).
  • Fond memories of reading Judith Krantz’s novels and fantasizing about jewels as a child (07:15, 19:13).
• Transition to Fine Jewelry
  • First fine pieces bought at Barneys and through New York vintage dealers (18:44).
  • Memories of collecting plastic gems as a child and playing “rich merchant’s daughter” (19:13).

Jennifer’s Approach and Philosophy

• Design, Provenance, and Story Over Big Diamonds
  • Prefers whimsical and artful pieces with personal histories, rather than simply large diamonds (07:08, 07:15).
  • “I see [old jewelry] as art. I’m not the kind of person that will go into Harry Winston and say, I want a diamond necklace or I want diamond earrings.” (06:38 - Jennifer Tilly)
• Provenance and Celebrity Relics
  • Cherishes owning pieces belonging to icons like Joan Crawford, Marlena Dietrich, Elizabeth Taylor, and even Marilyn Monroe dresses (22:30–36:18).
  • Capturing and preserving stories and legacies of jewelry and Hollywood items by documenting and possibly donating to museums (32:26–36:18).

Auction Tales and the Thrill of the Hunt

• Memorable Auctions and Near-Misses
  • Bidding wars for the Duchess of Windsor's famous Cartier Flamingo and other one-of-a-kind pieces (04:46–05:22).
  • “Sometimes I really want something. But, but if it’s not going for a good price, then I think like, well… I’m going to pass because it’s going for too much. And then those are the pieces that I look back on and I think … I should have got it because you’re never going to see it again.” (02:53)
• Jewelry as Investment and Losses
  • Debates practicality of jewelry as investment vs. romantic attachment (17:50–18:39).
  • The regret of selling significant pieces for financial reasons (18:39).

Collecting Philosophy and Advice

• Collect What You Love
  • “Go towards what you gravitate towards. If something is beautiful to you, then that’s the thing you should start to collect.” (44:33–45:50)
• Education and Buying Safely
  • Strongly suggests beginning with reputable auction houses (Sotheby’s, Christie’s) for authentic, quality pieces; warns of “charlatans” in the industry (43:25–44:33).
• On Having ‘Enough’ Jewelry
  • “Jewelry is art and jewelry brings me joy and everything is different. There’s new jewelers… every day. So it’s not like, wow, I really want that dress, but I didn’t get it. But you, it haunts you… But I don’t think that… you can ever say, okay, it’s enough.” (45:50–47:42)

Notable Quotes & Memorable Moments

• On Jewelry with a History

  • “All night long I had sparkly dreams that I was the most beautiful woman in the world, flying, desired by everyone, walking on the Via Veneto… It has memories. It soaked in all those happy memories of Elizabeth Taylor being in Rome and being in love. I really believe that all those memories came sparkling out of the brooch into my dreams.”
    — Jennifer Tilly (00:18 & 39:01)

• The One That Got Away

  • “A lot of these pieces, they only made one of them… you’re never going to see it again.”
    — Jennifer Tilly (02:53)

• On Wearing Her Own On the Red Carpet

  • “I want to be that person that says it’s mine, and I don’t have to say who I bought it from.”
    — Jennifer Tilly (28:12)
  • “In my early days, you borrow things and then you feel such an obligation… I just think… I mean, I know it’s how Hollywood works, but I just felt like sort of like a … [shrugs]. So now I hardly… I don’t think I borrowed any jewelry for a really long time.” (26:51–27:59)

• Jewelry as Living Art

  • “It gets sad when it’s sitting in the vault… It wants to be out in the world, sparkling and having a good time.”
    — Jennifer Tilly (39:01)

• On Building a Collection

  • “Anybody could go to Sotheby’s, Bonham’s, Doyle’s viewing. You can go, you can look at all the jewelry… I think that that’s a really good way to get an education.”
    — Jennifer Tilly (44:33–45:50)

• Why She Loves Brooches

  • “You have a black dress, it’s a frame for the brooch. The brooch always tells a story. You know, it’s an animal or a leaf or something or another. And so I love brooches.”
    — Jennifer Tilly (48:12)

• Her Dream Piece

  • “There was this… Serpenti bracelet, but it’s platinum and emeralds… it goes all the way up my arm… I’m kind of craving it.”
    — Jennifer Tilly (49:55)

Guide to Jennifer’s Collection: Highlights & Anecdotes

Costume and Designer Pieces

• Vintage Chanel
  • First Chanel necklaces embarrassing store experience—“Our clients are very discreet…” (12:13)
  • Autograph from Inès de la Fressange, Chanel muse (15:29)
• Dolce & Gabbana
  • Gondolier earrings and strawberry bracelet (10:23–11:41)
• Joan Crawford Charm Bracelet
  • Intimate piece with Oscars and lover charms, “like she’s collecting men” (22:30)
• Elizabeth Taylor Pieces
  • A yellow and white diamond brooch; a necklace Elizabeth herself wanted at auction (24:52–39:50)
• Dress from Marilyn Monroe
  • “Very high necked… filled with holes…” kept in original condition for history’s sake (33:24)
• Schiaparelli from Marlene Dietrich
  • Dress, cane (gift from Noël Coward), and a Hemingway letter—long tales behind each (31:48–36:15)
• Cole Porter–Commissioned Necklace
  • Aquamarine belt-buckle necklace for his wife (39:52)
• Bulgari ‘Serpenti’ Bracelets
  • “They go up your arm,” platinum and emerald design is her current fixation (49:55)

Mantra for Collectors

• Wear and Document Your Jewels
  • “It should be worn. It gets sad when it’s sitting in the vault… It wants to be out in the world, sparkling and having a good time.” (39:01)
  • Advises taking photos of yourself in pieces for provenance (38:10)

Timeline of Key Segments

• [02:20] – Jennifer’s dual passions: poker and jewelry
• [04:46] – Tales from the Duchess of Windsor’s famous auctions
• [08:42] – Jennifer’s life as an online auction “dealer” during the pandemic
• [11:59] – Costume jewelry days – Chanel and Haskell
• [17:50] – Reflections on buying for investment vs. love
• [20:28] – On Real Housewives: Who notices/understands fine jewelry
• [22:30] – Acquiring Joan Crawford’s charm bracelet
• [24:52] – Bidding war at the Elizabeth Taylor auction
• [27:59] – Why Jennifer rarely borrows for the red carpet
• [32:26] – Marilyn Monroe memorabilia: “he doesn’t love me”
• [36:15] – On donating to the Marlene Dietrich Museum, need for documentation
• [39:00] – Jewelry should live out of the vault; Elizabeth Taylor dreams
• [41:02] – Love for David Webb, JAR, and commissioning unique pieces
• [43:25] – Tips for collectors; avoid forgeries, learn at auctions
• [45:50] – Is there ever enough? No!
• [48:12] – Style notes: The brooch, the little black dress, and Hollywood accessorizing
• [49:55] – The next dream acquisition: Bulgari’s Polychrome Serpenti

Final Takeaways

Jennifer Tilly’s jewelry worldview is heartfelt, whimsical, and deeply rooted in storytelling. She collects for joy, adventure, memory, and beauty, prizing originality and provenance over mere carat size. Her tales—from childhood dress-up games to bidding battles for legendary jewels—infuse each piece with new life and meaning. As for jewelry collectors: seek knowledge, follow your taste, and wear your treasures, for jewels are “art, history, and joy” all at once.