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The 21st Century Best Costume Oscar Winners, Ranked

Costume design is rarely as analyzed as cinematography or sound in its effect on film storytelling but is often just as impactful; how characters present themselves and everything they’re trying to say or not say is often bound up in their clothing choices. Those choices are often the first thing we reach for in thinking about our favorite films. The sheer number of Cowboy Kens and Spider-Gwens out for Halloween this year (and also one very tiny Los Alamos employee who stopped by this writer’s trick-or-treating with their parents) is a testament to some of the great costume design work on display in 2023. So, the IndieWire Craft team decided to look back at the winners of the Best Costume Design Oscar since 2000 and see what we could learn about how costume design has evolved over the century so far.

The Academy certainly has a type. The Best Costume Oscar doesn’t reward films for muted contemporary looks, however telling and evocative those might be, but often honors the most elaborate costumes of a given year. A lot of the time that means rewarding the best a period has to offer, be it the flowing skirts and embellished embroidery of 18th- and 19th-century royal courts or the sharp gloss of a Hollywood tux in the ’20s. But it also applies to more fantastical worlds, too, whether that means the classic high fantasy of “The Lord of the Rings: Return of the King” or the Afro-Futurist wonder of Wakanda in “Black Panther” or the scavenger fever-dream of “Mad Max: Fury Road.” Best Costume Oscars reward costumes that go for broke (the way that only queens and emperors can).

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But within the cornucopia of different silks and artful tassels, the IndieWire Craft team found that Best Costume Oscar winners vary in terms of how costumes serve their film’s story. All display great craft. But the costume designs at the top of our list would’ve been wildly different movies in the hands of different costume designers. They bolster the setting and tone, work hand-in-hand with cinematography and production design to give the right color and texture (whether the film is black and white or not) that makes their film so vivid, and collaborate with the actors on telling us so much more about the characters than the script can. Read on for our takes on what each of the Best Costume Design Oscars did to sew up their award.

This piece contains contributions from Bill Desowitz, Jim Hemphill, Mark Peikert, and Wilson Chapman.

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