Kylie Jenner
Kylie Jenner’s revealing Roberto Cavalli wedding guest gown has a surprising celebrity fashion history Instagram/@kyliejenner

Kylie Jenner's headline-making wedding guest dress has a fashion history that goes back more than two decades. The Kylie Cosmetics founder wore a black vintage Roberto Cavalli cutout gown to Jordyn Woods and Karl-Anthony Towns' wedding in Malibu on 15 August 2026, but Celine Dion had already stepped out in the cream version of the same skin-baring design at the 2003 Billboard Music Awards.

The 'My Heart Will Go On' singer wore the Cavalli look on 10 December 2003 at the MGM Grand in Las Vegas, nearly 23 years before Jenner brought the silhouette back into the spotlight. Dion's version featured the same dramatic cutouts, embellished bands and floor-skimming skirt, transforming a dress now being debated as wedding guest attire into an early-2000s red carpet moment.

Kylie Jenner Revived the Vintage Cavalli Dress

Jenner, 29, attended Woods' wedding to New York Knicks star Karl-Anthony Towns alongside boyfriend Timothée Chalamet. Her vintage black Roberto Cavalli gown came from the designer's Spring 2004 collection, with a halter neckline, wide cutouts exposing the waist and hips, glittering embellished straps and a high centre slit. Vintage dealer Opulent Addict confirmed on Instagram that Jenner's gown had been purchased from its archive for the wedding.

The black colourway also fitted the apparent all-black dress code followed by guests at the Malibu ceremony, where Hailey Bieber, Justin Bieber, Michael B. Jordan and other attendees arrived in dark looks. The debate instead focused on the gown's revealing construction and whether a dress designed to make an impact on a red carpet was equally suited to a wedding. One Reddit user compared Jenner's vintage Cavalli gown to Fashion Nova, adding to the criticism surrounding her wedding guest look.

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Another commenter was more direct, writing: 'You're going to a wedding, not a club,' while arguing that the look did not fit their idea of black-tie wedding dressing. Others pushed back on that criticism, noting that celebrity weddings can operate under different fashion expectations from more traditional ceremonies. Jenner's dress nevertheless became one of the weekend's most discussed guest looks, despite technically following the wedding's black colour palette.

Céline Dion Wore It First in Cream

Dion's 2003 version shows just how dramatically styling and setting can change the effect of the same design. The five-time Grammy winner wore the cream Cavalli gown with platinum blonde curls, dangling diamond earrings and metallic heels at the Billboard Music Awards, where the cutouts and sparkling details were framed as red carpet glamour rather than wedding guest dressing.

Archival photographs from the night show the unmistakable silhouette more than two decades before its Jenner revival.

The timing is also a reminder of how quickly archival celebrity fashion has become part of the current wardrobe cycle.

Although Cavalli labelled the gown as part of its Spring 2004 collection, Dion was already wearing the cream version publicly in December 2003. Jenner's stylists Mackenzie and Alexandra Grandquist then brought the design back for one of 2026's biggest celebrity weddings, giving a 2000s Cavalli look a second high-profile life.

Same Dress, Two Very Different Moments

Side by side, the strongest similarity is the architecture of the gowns: plunging halter necklines, exposed sides, jewelled bands wrapping the body and long skirts broken up by a dramatic slit. The biggest difference is context. Dion wore cream to an awards show in 2003, while Jenner chose black for the wedding of one of her closest longtime friends in 2026.

The comparison has therefore turned Jenner's controversial wedding guest moment into an unexpected fashion archive discovery. Long before the dress prompted debates over what counts as appropriate wedding attire, Dion had already shown exactly what the Cavalli design looked like in its lighter, almost bridal-looking form.