Hailey Bieber's '90s Calvin Klein Dress Is the Opposite of Carolyn Bessette-Kennedy Minimalism

Same era, entirely different style.

Hailey Bieber wearing a calvin klein dress on the time100 gala red carpet
(Image credit: Getty Images)

Some fashion fans might see the Calvin Klein tags on Hailey Bieber's Time100 Gala gown and assume she's paying homage to Carolyn Bessette-Kennedy. But make no mistake: While her custom dress nods to the era defined by the late publicist (and subject of this spring's breakout drama, Love Story), it's much more aligned with Bieber's own approach to vintage styling.

The Rhode founder walked the April 23 red carpet in a maxi dress that fit her like a second, lacy skin. An overlay of metallic silver florals coated a skintone base, creating a painted-on effect. Calvin Klein confirmed in a press release that while the exact garment was made just for Bieber, it's modeled off another gown that walked its Spring 1992 runway.

Hailey Bieber wearing custom Calvin Klein on the Time100 Gala red carpet

Hailey Bieber arrives at the Time100 Gala in a custom Calvin Klein dress, inspired by a Spring 1992 design.

(Image credit: Getty Images)

1990s Calvin Klein was as known for its campaigns starring the likes of Kate Moss as the women behind the scenes: namely, Carolyn Bessette-Kennedy and Kelly Klein. But CBK, whose name is shorthand for an exacting form of minimalism, probably would have steered a VIP client toward Bieber's metallic florals instead of wearing them herself. She preferred a more constrained, black-and-white palette, as well as less revealing silhouettes. And while she made the press office at Calvin Klein run, her own rare red carpet appearances often included pieces from Yohji Yamamoto, Jean Paul Gaultier, or Versace.

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If Hailey Bieber's Calvin Klein dress was making another reference, it was to the beauty mogul herself. With help from her longtime stylist, Dani Michelle, Bieber's vintage 1990s pulls often feature tight-hugging silhouettes and flirty touches of lace. Just last weekend at Coachella, she flipped the script on business founder dressing in a vintage Dior slip circa 1999 for a Rhode activation. She's also the proud owner of a sequin Bob Mackie dress (worn on the celebrity birthday party circuit) and a vintage Versace leather jacket (which she's even loaned to Kylie Jenner).

It's on the beauty and accessories front where Bieber and Bessette-Kennedy have more in common. Posing with honorees like Dakota Johnson and LISA, Bieber showed off a middle-parted blowout and nude nails—an understated look CBK often wore herself.

Hailey Bieber with Dakota Johnson on the Time100 Gala red carpet

Bieber posed with honoree Dakota Johnson on the red carpet.

(Image credit: Getty Images)

To finish, Bieber only added a Cartier watch and Briony Raymond diamond earrings alongside her engagement ring. That sort of accessory restraint is exactly what CBK would have done.

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Halie LeSavage
Senior Fashion News Editor

Halie LeSavage is the senior fashion news editor at Marie Claire, leading coverage of runway trends, emerging brands, style-meets-culture analysis, and celebrity style (especially Taylor Swift's). Her reporting ranges from profiles of beloved stylists, to exclusive red carpet interviews in her column, The Close-Up, to The A-List Edit, a newsletter where she tests celeb-approved trends IRL.

Halie has reported on style for eight years. Previously, she held fashion editor roles at Glamour, Morning Brew, and Harper’s Bazaar. She has been cited as a fashion expert in The Cut, CNN, Puck, Reuters, and more. In 2022, she earned the Hearst Spotlight Award for excellence in journalism. She holds a bachelor’s degree in English from Harvard College. For more, check out her Substack, Reliable Narrator.