Last year, Sotheby’s wowed the fashion set with its record-breaking auction of Princess Diana’s iconic sheep sweater, proving that royal style is always in vogue. This year, the auction house is doubling down on its fashion prowess, spotlighting the American fashion icon Carolyn Bessette-Kennedy alongside an unexpected twist — NFL legend Tom Brady.
The festivities for the auction began with an exclusive cocktail party in New York City, where chic collectors sipped martinis and admired pieces that epitomized Bessette-Kennedy’s simple elegance and Brady’s all-American finesse. It’s a sartorial twist worthy of the runway — Diana’s style legacy may have passed the crown, but Carolyn and Tom are now sharing the throne.
Returning for its second edition, Sotheby’s annual Fashion Icons sale reaffirmed its role as a must-watch event, celebrating the timeless influence of fashion’s most iconic figures and offering a glimpse into the lives of those who left an indelible mark on style.
Carolyn Bessette-Kennedy: The Embodiment of Quiet Luxury
The Fashion Icons sale shined its spotlight on three garments from Carolyn Bessette-Kennedy’s personal collection — her first public fashion offering, making waves among collectors. Revered for her minimalist aesthetic and effortless elegance, Bessette-Kennedy’s impact on ’90s fashion is as enduring as ever. The pieces were consigned by her close friend Rosemarie Terenzio, who affectionately called Bessette-Kennedy her “fashion fairy godmother.”
Stealing the show was a vintage faux-leopard double-breasted coat from circa 1969, estimated at $20,000–$30,000. Gifted to Terenzio, the coat was worn on a memorable first date, embodying the generosity and stylish boldness that defined Bessette-Kennedy. With its retro flair reminiscent of Prada’s Autumn/Winter 1996-97 collection, the coat also carried a historical nod to the era’s embrace of eclectic glamour.
Another standout was a Prada single-breasted black wool coat from 1997, valued at $15,000–$20,000, worn by Bessette-Kennedy to Bill Clinton’s second inauguration. This coat, in its understated polish, captured the essence of quiet luxury. Her Yohji Yamamoto black wool jacket paired with a Junya Watanabe skirt added an avant-garde touch, further solidifying her status as an unwavering style muse.
“These garments reveal a woman who navigated public scrutiny with intelligence and grace,” said Sotheby’s Fashion Specialist Lucy Bishop, emphasizing Bessette-Kennedy’s mastery of tailored simplicity and sophistication.
Tom Brady’s GOAT Collection: Watches and Treasures
Complementing the fashion auction, Sotheby’s unveiled GOAT Collection: Watches and Treasures from Tom Brady, featuring 41 meticulously curated items chronicling Brady’s legendary 28-year career. The pièce de résistance? A Rolex Daytona ‘John Player Special’ — a yellow gold chronograph wristwatch estimated at $600,000–$900,000. Brady sported this rare timepiece at the New England Patriots’ 2023 season opener, adding sentimental value to its already sky-high allure.
The collection also included a Patek Philippe Grand Complication, estimated at $200,000–$400,000, a nod to Brady’s appreciation for fine craftsmanship beyond the football field. Reflecting on his collection in Sotheby’s Magazine, Brady said, “Time is everything… I’m recognizing that others will cherish these items as I have.”
A Testament to Legacy
This year’s Fashion Icons sale wasn’t just about exquisite fashion and luxury timepieces; it was a tribute to the legacies of two icons who defined their respective worlds. Bessette-Kennedy’s perennial grace and Brady’s unparalleled sportsmanship made for a captivating juxtaposition, reinforcing Sotheby’s dedication to preserving the stories of cultural giants.
Online bidding continues until December 17, with the garments and treasures on public display at Sotheby’s New York from December 5–10. This year’s auction promises to etch its mark on the fashion and collectibles world, where elegance, influence, and legacy take center stage.
