How to Recreate Carolyn Bessette Kennedy’s Best ’90s Outfits

Long a fixture of style mood boards, Carolyn Bessette Kennedy’s outfits are receiving a new wave of attention, thanks to Ryan Murphy’s Love Story: John F. Kennedy Jr. and Carolyn Bessette. The biographical anthology (streaming on Hulu beginning February 12) centers on the couple’s high-profile romance, tracking the socialite’s minimalist ’90s style along the way.

Thirty years on, Bessette Kennedy’s neutral palette, restrained styling, and rejection of visible designer logos feel attuned to today’s quiet luxury crowd. Season after season, she remains a muse for minimalist labels like Toteme, The Row, and Calvin Klein, where she worked as a publicist.

In celebration of Bessette Kennedy’s timeless style, we’ve recreated seven of her most iconic ’90s outfits below. Built around practical staples and smart designer investments, these versatile looks will feel just as chic decades on as they do today.

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Signature Accessories

Bessette Kennedy’s casual outfits were often finished with a tortoiseshell headband and slim oval sunglasses. Ray-Ban and Camila offer styles similar to the Selima Optique frames and Charles J. Wahba hair accessories she favored. Her bootcut Levi’s jeans mark another signature piece still available for purchase today.

Mixed Neutrals

Few style icons maintain such a high level of restraint. Sticking to understated silhouettes and solid neutrals allowed Bessette Kennedy to rebel against more subtle fashion conventions, such as mixing black and brown.

“She didn’t have a strategy; she wore what she felt, and her intuition would drive her,” designer Gabriela Hearst writes in her foreword for CBK: Carolyn Bessette Kennedy: A Life in Fashion. “She understood the value of quality and moderation.”

A Quiet Luxury Coat

The belted black Prada coat from Bessette Kennedy’s personal closet was recently valued at $20,000 at a Sotheby’s auction. Featured in many of the socialite’s most famous looks, it’s all but guaranteed to be recreated in the new FX series, leading trend forecasters to predict similar outerwear styles will rise in popularity this fall.

All-Black Evening Attire

Bessette Kennedy’s formal wardrobe is well-documented—and quite easy to recreate for an upcoming special occasion you may be shopping for. From political appearances to benefit dinners, she almost always wore all black, often with an off-the-shoulder silhouette and a simple satin clutch.

An Effortless White Shirt

One of Bessette Kennedy’s most celebrated looks is a white Yohji Yamamoto button-up shirt and black silk maxi skirt, worn to a fundraising gala at the Whitney mere months before her tragic death in 1999.

“In short, the shirt was her magnum opus in simplicity,” Sunita Kumar Nair writes in CBK: Carolyn Bessette Kennedy: A Life in Fashion. “Her friends spoke of her instinctive ability to style a shirt in multiple ways: folding both ends of the shirt or making a criss-cross like her Whitney ensemble; tucking one shirt end into her trousers and leaving the other end out; or unbuttoning the top button down to show her décolletage. There was no end to how Carolyn made the shirt hers.”

Intentional Minimalism

Bessette Kennedy’s summer style is less well-known, but paparazzi photographs from the mid-1990s suggest an intentional minimalist approach. Think cropped bootcut jeans, sleeveless knit tops, and strappy sandals—and on occasion, an heirloom Cartier Tank or Hermès Birkin.

An Investment Bag

The socialite’s handbag collection has long been a subject of fascination—so much so that in 2022, Prada released the 1995 Re-Edition Bag, a version of the boxy shoulder bag that Bessette Kennedy carried for years.

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