Fashion

The Most Stylish Movies of the '90s, Ranked

A thoroughly unscientific (but nonetheless authoritative) appraisal of the decade's best-dressed films.
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There's no doubt that '90s nostalgia is at a high point. Over all of this, of course, looms fashion, which is always keenly attuned to, if not outright governed by, deeper cultural trends—and if that means a galvanic '90s menswear comeback, so be it. To meet the decade's revival, let's take a look back through the archives to find the most stylish movies of the decade.

14. Wayne's World


Long hair, trucker hats, and graphic tees. It's everything a '90s kid could dream of.

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13. Clueless


    

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When it comes to influential womenswear in movies, Clueless takes the cake. But there's some good menswear inspiration, too—like the combo of short jackets and high-waisted pants.

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12. Boogie Nights


    

OK, it's a bit of a cheat because it's set in yet another decade. But Paul Thomas Anderson's take on '70s sleaze is about as good-humored in its approach to the fashion of the era as you'd expect, which may account for its uneasy but stylish characters, who retain their appeal even at their most ludicrous. Bring back these collars, please.

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11. Reservoir Dogs


    

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The charismatic antiheroes of Reservoir Dogs are draped in all-black suits for much of the movie, rendering the gang's stylish, slo-mo saunter from diner to cars instantly iconic.

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10. White Men Can't Jump


   

Woody Harrelson and Wesley Snipes are the street style heroes we need.

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9. The Big Lebowski


    

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The Big Lebowski is a touchstone for every man who's ever worn a robe outdoors and that's enough for us. The Dude never wore a tailored suit or slick designer threads but he embodied the spirit of athleisure before that was even a word. Also: that sweater.

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8. Fight Club


    

Fight Club proves itself eminently stylish, playing Brad Pitt's sleezy, '90s post-rave look against Ed Norton's drab office drone uniform. The red leather jacket really says it all.

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7. Fear and Loathing in Las Vegas


   

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This is the most iconic bucket hat since Gilligan's Island. Plus, camp-collar shirts have yet to meet their maker.

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6. Empire Records


   

Don't record store employees always seem to have the best style? Just look at that cardigan layering game.

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5. Romeo and Juliet


   

It's Leo as Romeo skulking around floral-print shirts and, when the occasion calls for it, suits with floral-print ties. Basically a crystal-ball look at how guys dress in 2017. Need we say more?

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***

4. Juice


    

This is a movie with some of the most influential style of the decade, setting the template for hip-hop and street fashion for years to come.

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3. The Talented Mr. Ripley


   

In The Talented Mr. Ripley, Jude Law confirmed himself as one of Hollywood's most fashionable actors, traipsing through Italy with effortless panache. (Yes, it's set in the '50s. And yes, we're still including it on this list because it's so damn good.) But Matt Damon's dorky sociopath, Tom Ripley, is no sartorial slouch himself, and soon learns the rules of the high-fashion game.

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2. Dazed and Confused 


   

Another cheat from the '70s but still—so good. Tucked in graphic tees. Weed leaves. Matthew McConaughey. Everything about this movie's costume design was impeccable. Alright, alright, alright.

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1. Trainspotting


Every single guy in this photo would look right at home in the current era. And not just at home, but really damn cool. If there's anything better than '90s style, it's British '90s style. These are exhibits A through D.

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This story originally appeared on Esquire.com. Minor edits have been made by the Esquiremag.ph editors.

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