Minimalism, Legacy, and the 90s Revival

In the pantheon of late 20th-century style, few figures remain as enduring, or as studied, as Carolyn Bessette Kennedy. At a moment when fashion was often defined by excess, she distilled her wardrobe to its most essential elements: impeccable tailoring, a disciplined neutral palette, and silhouettes that felt at once modern and timeless. Her aesthetic, quiet, deliberate, and unmistakably New York, helped define 1990s minimalism and continues to influence designers, stylists, and collectors today.
That legacy now takes center stage in Exceptional Fashion: including items from the wardrobe of Carolyn Bessette Kennedy, presented by The Fashion Auctioneer. The sale represents the most comprehensive collection assembled to date dedicated to her iconic style. At its core are four historically significant pieces from Carolyn’s personal wardrobe, gifted to her close friend Rosemarie Terenzio, longtime assistant and confidante to John F. Kennedy Jr.. Privately preserved for more than twenty-five years and entering the market for the first time, these garments offer exceptional rarity and direct provenance.
Their importance extends beyond personal ownership. These were among Carolyn’s favored pieces, garments repeatedly worn and photographed during defining public moments in mid-to-late 1990s New York. In an era before social media, when style circulated through candid street photography and cultural events, her wardrobe became a visual shorthand for intellectual minimalism and understated confidence. Today, amid a resurgence of 1990s fashion and renewed cultural fascination through contemporary television and media portrayals, her influence feels not nostalgic but remarkably current.
For collectors, this sale offers more than beautifully preserved examples of Prada and Yohji Yamamoto. It presents an opportunity to engage directly with a defining chapter of American fashion history, where personal style, public mythology, and enduring design converge.

Featured Auction Highlights: 

Prada camel wool pencil skirt, Fall-Winter 1996-97
On October 6, 1996, just weeks after her wedding, Carolyn stood beside JFK Jr. outside their Tribeca apartment wearing a camel pencil skirt for her first public appearance as Mrs. Bessette Kennedy. (View the Getty image HERE.)
The camel wool pencil skirt by Prada reflects the brand’s mid-90s intellectual minimalism. Clean lines, impeccable tailoring, and a neutral palette made this silhouette a cornerstone of Carolyn’s wardrobe.
In her hands, the pencil skirt was urban armor. Paired with a simple knit or tailored coat, it epitomized the quiet authority that defined her post-wedding public appearances.

Lot 8
Description: labelled, size 40, with double-faced seams, sitting low on the waistline, waist 28in, 71cm, length 29in, 74cm, together with a pair of Prada chestnut-brown leather knee-high boots, 1996, size 38.5, calf 7in,18cm across very top, and a non-associated black wool sweater, modern (4)
Auctioneer Note: Provenance: These items were acquired in 2017 by a private collector, purchased directly from one seller discovered on E-bay. The first two pieces they acquired were the Prada camel skirt (Lot 8) and Prada camel coat (Lot 14). These items were described 'as seen on Carolyn Bessette Kennedy'. The collector was later told by the seller that these items were believed to have originally belonged to Carolyn Bessette Kennedy and that they had been acquired from a former George magazine staffer in 2011. 
Estimate: $2,000 - $3,000

Yohji Yamamoto black silk-wool skirt, 1990s
At the Whitney Museum Gala on March 9, 1999, celebrating The American Century: Art and Culture 1900–2000, Carolyn appeared in a fluid black skirt that captured her affinity for architectural drape. (View the Getty image HERE.)
Designed by Yohji Yamamoto, the piece speaks to her embrace of Japanese minimalism. Yamamoto’s cerebral tailoring and subtle asymmetry aligned perfectly with her understated glamour.
While others leaned into late-90s embellishment, Carolyn chose depth over decoration, proving that black, in the right cut, is never basic.

Lot 13
Description: labelled, size S,  with tiers of ruffles to front hem, waist 28in, 71cm, hip 38in, 96cm, length 45in, 114cm; together with a Whiting & Davis gilt oroton mesh purse, probably 1950s, labelled; and a non-associated white cotton shirt, modern (3).
Auctioneer Note: Auctioneer Note: Provenance: These items were acquired in 2017 by a private collector, purchased directly from one seller discovered on E-bay. The first two pieces they acquired were the Prada camel skirt (Lot 8) and Prada camel coat (Lot 14). These items were described 'as seen on Carolyn Bessette Kennedy'. The collector was later told by the seller that these items were believed to have originally belonged to Carolyn Bessette Kennedy and that they had been acquired from a former George magazine staffer in 2011. The vintage Whiting & Davis bag was later acquired by the collector and the white shirt is a contemporary edition to the ensemble. Only the skirt was acquired with the other pieces in the collection in 2017. 
Estimate: $500 - $800

Carolyn Bessette Kennedy's Prada single-breasted coat, 1996
This particular Prada coat was a favorite of Carolyn Bessette Kennedy and stands among her most iconic and important wardrobe pieces. Defined by its sharp single-breasted tailoring and absence of ornamentation, it encapsulates the disciplined minimalism that made her a defining style figure of the 1990s.
She is memorably photographed wearing the coat on March 15, 1997 (view the Getty image HERE). In another widely circulated moment, she is pictured walking through Tribeca with her husband, John F. Kennedy Jr., and their dog on October 1, 1998 (see that Getty image HERE). In these candid street scenes, the coat becomes more than outerwear; it becomes part of her visual signature. 
Photographed against the backdrop of downtown Manhattan, the coat helped cement a new model of American elegance, private yet powerful, modern yet timeless. Today’s revival of streamlined wool coats and pared-back tailoring on international runways owes much to images like these, where simplicity itself became the statement.

Lot 2
Description: labelled, size 42, camel double-faced wool-angora, two flap pockets to chest and two slit pockets to hips, matching belt with faux tortoiseshell 'Prada' buckle, un-lined, bust 36in, 91cm, shoulders 16in, 40.5cm, sleeve 25in, 63cm, length 41in, 104cm
Auctioneer Note: The epaulettes have been removed. Carolyn is photographed on numerous occasions wearing this example and other variations of the same style, including in black and red tweed. This design is probably from Prada's Autumn-Winter 1996-97 collection which featured coats and skirts in a slim silhouette, heavily influenced by designs from the late1960s-early 70s.
Estimate: $20,000 - $30,000

Carolyn Bessette Kennedy’s Yohji Yamamoto Little Black Dress, 1990s
Gifted by Carolyn Bessette Kennedy to her close friend Rosemarie Terenzio, this Yohji Yamamoto Little Black Dress embodies one of the most consistent through-lines in Carolyn’s wardrobe: disciplined devotion to black.
She wore the dress on March 5, 1998, to attend an event marking the anniversary of the Apollo space program, view the images from the evening HERE and HERE.
The Little Black Dress was a cornerstone of her personal uniform, particularly designs by Yohji Yamamoto, whose cerebral approach to tailoring aligned seamlessly with her aesthetic. At first glance, the silhouette is simple and demure; on closer inspection, the oversized collar introduces a sculptural element.
The choice of black itself was more than aesthetic. In New York, black functions as both armor and identity. As journalist Amy Larocca wrote in New York Magazine, “We wear black because we’re not tourists…because we are, in a sense, with the band. The band is New York, and the color is black.” Yamamoto himself has observed, “Black is modest and arrogant at the same time… but above all, black says this: ‘I don’t bother you, you don’t bother me.’”
Few garments capture that ethos more completely. In Carolyn’s hands, the Little Black Dress was not simply eveningwear, it was a statement of belonging, privacy, and intellectual elegance.

Lot 3
Description: labelled, size S, twill wool, with oversized collar, concealed front zipper and two flap pockets to hips, bust 34in, 86cm, waist 30in, 76cm, length 43in, 106cm
Estimate: $15,000 - $20,000

Beyond celebrity provenance, this sale underscores a larger cultural shift. The 90s revival, seen across runways, resale platforms, and television, reflects a renewed appetite for clarity in design. Carolyn’s wardrobe, once captured by paparazzi on Manhattan sidewalks, now reads as a masterclass in restraint.

Presented by The Fashion Auctioneer, Exceptional Fashion: including items from the wardrobe of Carolyn Bessette Kennedy will be offered as a timed auction from February 13, 2026 at 2PM ET through March 3, 2026 at 10AM ET. The sale brings together the most comprehensive collection assembled to date dedicated to her iconic style, anchored by four historically important pieces from the personal wardrobe of Carolyn Bessette Kennedy.

For collectors, these garments represent more than beautifully preserved examples of 1990s design. They mark a singular convergence of American cultural mythology and European avant-garde fashion, where downtown minimalism became a global aspiration. 

View the full auction catalog and register to bid on Bidsquare.com.