In the 1990s, few couples captured the public imagination more than John F. Kennedy, Jr. and Carolyn Bessette-Kennedy. He was the son of U.S. president John F. Kennedy and she was a publicist for Calvin Klein. Their shared good looks made them magnets for the paparazzi, but so did Bessette-Kennedy’s unimpeachable style—effortlessly cool and elegant, in neutral hues—that set the tone for the era’s minimalist chic. She was embraced as America’s answer to Princess Diana.

John and Carolyn wed in 1996, two years after a meet-cute in a Calvin Klein dressing room. Their marriage and lives, however, were tragically cut short by a plane crash in 1999. Still, Bessette-Kennedy’s fresh-faced poise and crisp cool have seen her endure in books, Instagram accounts, and fashion mood boards as a style icon for the ages.

“There’s a timelessness about her and that’s her appeal,” Sunita Kumar Nair, author of CBK: Carolyn Bessette-Kennedy: A Life in Fashion, noted in an interview. “There’s no label to put on her. She never put a label on herself, she’s this open canvas that you can interpret what you want from her looks.”

Bessette-Kennedy’s Vintage Double-Breasted Faux-Leopard Fur Coat. Photo: Sotheby’s.

These same qualities are evident from Bessette-Kennedy’s extensive wardrobe, a small slice of which is going up for an auction by Sotheby’s, set to run from November 27 until 17 December as part of the company’s annual “Fashion Icons” event in New York City.

The auction, which will take place online, includes three pieces of clothing that Bessette-Kennedy gave to her close friend Rosemarie Terenzio, a best-selling author, executive producer, and fashion icon in her own right.

Prada Single-Breasted Black Double-Faced Wool Coat. Photo: Sotheby’s.

Each piece is more striking than the last, and each has a story to tell. Bessette-Kennedy’s vintage, double-breasted, faux-leopard fur coat, valued at $20,000 to $30,000, was given to Terenzio to wear on a date. “Whenever I had a date, Carolyn would say, ‘What are you wearing?’” the latter recalled in her 2012 book, Fairy Tale Interrupted: A Memoir of Life, Love and Loss, which describes Bessette-Kennedy as a “fashion fairy godmother.”

The second piece of clothing, a single-breasted, black, double-faced wool coat by Prada from 1997 valued between $15,000 and $20,000, was one of Bressette-Kennedy’s personal favorites. It showed up in several paparazzi and red carpet pictures taken over the course of her short life, including on the day she and her husband left their Tribeca apartment to attend Bill Clinton’s presidential inauguration.

Yohji Yamamoto Black Wool Double-Breasted Jacket. Photo: Sotheby’s.

Last but not least, Sotheby’s is selling a black wool double-breasted jacket designed by the Japanese fashion designer Yohji Yamamoto. Labeled size XS and valued between $15,000 and $20,000, Bessette-Kennedy wore this item to 1997’s Jacqueline Kennedy Onassis Medal event, which that particular year was held in honor of actor Robert DeNiro.

“Carolyn has left an indelible mark on fashion and on those who knew her,” Terenzio said in a statement. “Her pieces are symbols of a woman that continues to inspire style and captivate the public’s imagination. These historical pieces deserve to be cherished and properly preserved, to honor Carolyn’s legacy and ensure she is remembered.”