Hailey Bieber and Kendall Jenner Do Dior, Decades Apart, at W’s Pre-Oscars Dinner

Oscars weekend kicked off last night in Los Angeles with W Magazine and Dior’s pre–Academy Awards dinner, corralling a who’s-who of Hollywood, fashion, and film—many of whom arrived outfitted in Jonathan Anderson’s Dior designs. But leave it to models and close friends Hailey Bieber and Kendall Jenner to offer two distinct takes on the house’s past and present: while Bieber opted for one of Anderson’s “new” looks, Jenner threw it back to the supermodel era with a vintage piece from the 1990s.

Bieber mixed a classic French silhouette with an American staple, pairing a cropped Bar Jacket from Anderson’s debut spring 2026 Dior show with bootcut jeans that sat low on her waist. The Rhode mogul paired the high-low combination with strappy black heels and minimal jewelry.

Look familiar? Harry Styles wore the exact blazer, paired with slouchy dark jeans and those infamous mint green ballerina slippers, at the 2026 Grammys in February which Hailey attended with her husband, Justin Bieber.

Although Jenner also opted for Dior separates, her look drew from the house’s archives, coming from John Galliano’s era. The runway star went a lingerie route with a lace-trimmed camisole from Galliano’s fall 1998 show for Dior. She kept styling sleek, accenting her archival find with a thin black scarf, pleated trousers, and classic high heels.

Many of the evening’s attendees, from Oscar nominee Teyana Taylor to stars like Odessa A’zion and Charlize Theron, were outfitted in pieces from Anderson’s spring and fall Dior shows—the latter of which was just unveiled at Paris Fashion Week earlier this month. Yet Bieber and Jenner offered two distinct visions of Dior. One brand new, albeit with roots in the house’s past, and the other pulled straight from the archives.