Good Taste Never Goes Out of Style: The Fashion Auctioneer’s Exceptional Fashion: Including Items From The Wardrobe of Carolyn Bessette Kennedy Sale

Carolyn Bessette Kennedy (American, 1966-1999) the wife of John F. Kennedy Jr. (American, 1960-1999), was known for her signature style which included clean lines, neutral colors, and form fitting designs. Her fashion choices, developed over her career starting at Calvin Klein in the late 1980s, projected confidence and self-protection at the same time. The Fashion Auctioneer of Richmond, VA presented its 24 lot Exceptional Fashion: including items from the wardrobe of Carolyn Bessette Kennedy timed auction which closed on March 3, 2026. The sale generated spectacular results, reflecting the public’s ongoing interest in the late socialite more than a quarter century after her tragic passing. Here are some highlights from that small but well curated event. All prices noted include the auction house’s buyer’s premium. 

Coats were a key category in this sale, with all producing impressive results. The top lot in this sale was #2, Carolyn Bessette Kennedy’s Prada single-breasted coat from 1996. Estimated at $15,000-30,000, it traded hands at $192,000 and generated 29 bids. This size 42, camel colored, double-faced wool-angora example was detailed with two chest flap pockets, two hip slit pockets, and a matching belt with an imitation tortoiseshell ‘Prada’ buckle. It was her signature winter outwear and one of her favorite items in her wardrobe. According to The Fashion Auctioneer’s experts, “This design is probably pre-collection, Autumn-Winter 1996-97, which featured coats and skirts in a slim silhouette, heavily influenced by designs from the late 1960s-early 70s.”

This sale also featured a number of Bessette Kennedy’s skirts. Lot #8, a Prada camel wool pencil skirt, was estimated at $2,000-3,000, had 30 bids, and generated $30,000. This size 40 skirt featured double faced seams and was from Prada’s Fall-Winter 1996-97 line. The skirt was also sold with a black wool sweater and a pair of black leather boots. According to The Fashion Auctioneer’s experts, “Carolyn Bessette Kennedy is famously photographed wearing an identical skirt, October 6th, 1996, carefully chosen for her first public appearance as Mrs. Bessette Kennedy.”

Prada, an Italian fashion house started in 1913 as a luxury leathergoods manufacturer, is known today for its subtle color palate, structured, minimalist construction and detailing, and use of exquisite fabrics and materials. Carolyn Bessette Kennedy loved the Prada aesthetic, and integrated pieces from the company’s lines into her everyday as well as special occasion outfits. Her fashion choices leaned towards Prada after her marriage to John F. Kennedy Jr. in 1996. Prada’s understated elegance was a perfect complement to Bessette Kennedy’s new role as a very public – and very photographed – celebrity.

The “little black dress” was one of Carolyn Bessette Kennedy’s signature wardrobe items, and this event offered several from a variety of designers. Lot #3, Yohji Yamamoto’s little black dress, was estimated at $10,000-20,000, generated 5 bids, and realized $20,000. This 1990s-era classic was a size small, made of black twill wool, and finished with a statement collar, hidden front zipper, and two flap pockets. According to The Fashion Auctioneer’s experts, “Carolyn wore this dress to attend an event marking the anniversary of the Apollo space program on March 5th, 1998.”

Carolyn Bessette Kennedy also favored flattering, contemporary two piece suits for her public appearances. Lot #17, a Yohji Yamamoto two-piece ensemble, was estimated at $2,000-3,000, generated 9 bids, and traded hands at $8,750. This 1990s-era black wool suit was labeled size small; the jacket had a nipped waist and a deep “v” front,  and the skirt was full length and slightly flared. According to The Fashion Auctioneer’s experts, “Carolyn Bessette Kennedy wears an identical ensemble and scarf, accessorized with a cloche, to attend the opera in Italy, 1997.”

Designer Yohji Yamamoto (Japanese, b. 1943) is best known for his unconventional, geometric, and minimalist aesthetic – usually executed in black fabrics and materials. His gender-neutral designs often feature architectural-inspired elements, such as the statement collar on the dress highlight, and the jacket front on the suit highlight. Carolyn Bessette Kennedy favored Yamamoto’s garments in the mid to late 1990s, and often wore his designs to high-profile functions. 

This sale rounded out with a variety of outerwear selections as well as handbags owned by Carolyn Bessette Kennedy. Lot #16, a Prada black patent leather bag, was estimated at $400-600, generated 40 bids, and traded hands at $9,375. This purse was marked Prada, had narrow shoulder straps, a zipper top, and measured 10 x 9-1/2 x 3-1/2″.

For more information on The Fashion Auctioneer’s March 3, 2026 Exceptional Fashion: including items from the wardrobe of Carolyn Bessette Kennedy sale, please see https://bid.thefashionauctioneer.com/auctions/the-fashion-auctioneer/exceptional-fashion-including-items-from-the-wardrobe-of-carolyn-bessette-kennedy-22420.