Few figures in fashion history embody the phrase “iconic” as perfectly as Carolyn Bessette-Kennedy. Renowned for her minimalist style and embodiment of “quiet luxury,” Ms. Bessette-Kennedy captivated the world with her understated elegance. As a publicist for Calvin Klein and later as the wife of John F. Kennedy Jr., she became a beacon of 1990s American fashion. Even 25 years after her tragic passing, her influence continues to inspire.
the “Profile in Courage Awards”, 1998
This December, Sotheby’s pays tribute to her enduring legacy with three exclusive garments from her personal collection, offered during the second annual Fashion Icons auction in New York. These rare pieces, gifted to her close friend RoseMarie Terenzio, will be displayed at Sotheby’s New York from December 5 to 10, with online bidding open from November 27 to December 17.
The garments, each steeped in personal memories, reflect the deep bond between Ms. Bessette-Kennedy and Ms. Terenzio, who was John F. Kennedy Jr.’s executive assistant and confidante. As Ms. Terenzio fondly recounts in her bestselling memoir Fairy Tale Interrupted: A Memoir of Life, Love and Loss, Ms. Bessette-Kennedy acted as her “fashion fairy godmother.”
One standout piece is a vintage double-breasted faux-leopard fur coat dating back to 1969, gifted to Ms. Terenzio during a conversation about a first-date outfit. “It looks perfect on you. You should keep it. I’ve been photographed in it so many times [the media] will start making fun of me,” Ms. Bessette-Kennedy had said. The coat, with its bold print and practical design, encapsulates her ability to merge practicality with polished sophistication. This striking piece, with an estimated value of $20,000 to $30,000, was a favorite of both women and remains a symbol of Carolyn’s playful generosity.
The auction also includes a sleek Prada single-breasted black double-faced wool coat from 1997, epitomizing Ms. Bessette-Kennedy’s signature refined style. She wore the dress at both Bill Clinton’s inauguration and for casual strolls through TriBeCa. With its tailored silhouette and retro influences, the coat is estimated at $15,000 to $20,000.
Another highlight is a Yohji Yamamoto black wool double-breasted jacket, paired with a Junya Watanabe for Comme des Garçons skirt. She wore the jacket to the Jacqueline Kennedy Onassis Medal event in 1997. “Carolyn’s wardrobe tells the story of a woman who navigated the bustling streets of New York and exclusive soirées with equal grace,” says Lucy Bishop, Sotheby’s Fashion Specialist. “Her choices were practical yet polished—reflecting the power of understated elegance. These garments capture the essence of a remarkably normal yet extraordinary woman whose legacy continues to inspire modern fashion.”
Ms. Terenzio’s decision to partner with Sotheby’s is a nod to the auction house’s history of preserving the Kennedy legacy. These pieces stand as enduring reminders of Carolyn Bessette-Kennedy’s unmatched style and grace.
