14. Wayne’s World
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.
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.
11. Reservoir Dogs
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.
10. White Men Can’t Jump
Woody Harrelson and Wesley Snipes are the street style heroes we need.
9. The Big Lebowski
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.
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.
7. Fear and Loathing in Las Vegas
This is the most iconic bucket hat since Gilligan’s Island. Plus, camp-collar shirts have yet to meet their maker.
6. Empire Records
Don’t record store employees always seem to have the best style? Just look at that cardigan layering game.