The Best Oscars Red Carpet Looks of All Time

Hailed as Hollywood’s biggest night, the annual Academy Awards have become a pillar of pop culture. With a near-century-long legacy, the prestigious soiree celebrates the silver screen, reflects the cultural mood of the moment, and, of course, serves as a playground for boundary-breaking fashion. Much like the transportive power of film, the Oscars red carpet is a hub for imaginative sartorial world-building.

Over the years, it has been filled with gorgeous gowns, to be sure. But at its best, it’s also been delightfully weird, unexpected and conversation-sparking. In 2001, Björk turned heads in a now infamous swan dress. Since the ’70s, Diane Keaton has been eschewing the norms of feminine frocks in menswear suits. Back in 1998, Sharon Stone caused a stir when she showed up in an oversized T-shirt from Gap—which was reverently referenced by Zendaya over a decade later.

Last year, the Oscars red carpet delivered a fresh set of memorable style moments. Timothée Chalamet fancied frilly scarves while promoting A Complete Unknown. Sing Sing star Coleman Domingo continually pushed the boundaries of menswear through opulent overcoats and accessories. Cynthia Erivo, fresh off a viral Wicked press tour, delivered some method-dressing magic. Doja Cat stunned in a Balmain leopard-print mermaid gown, and Andrew Garfield arrived wearing a chocolate-brown Gucci silk suit.

Prev

Next

Photography courtesy of Getty Images

1/2

Doja Cat in Balmain at the 97th Academy Awards, 2025

Last year’s Oscars red carpet proved that simple looks can be striking. And with the 98th Academy Awards set to take place this Sunday, new trends and sartorial narratives are set to emerge. In anticipation, we’ve rounded up the best Oscars red carpet moments of all time below.

Prev

Next

Photo by Mirek Towski/FilmMagic

1/62

Björk in Marjan Pejoski at the 73rd Academy Awards, 2001

With additional files and text by Hadiqah Khalil.