To me, Mariel Hemingway's outfits in Manhattan are so much better than Diane Keaton's in Annie Hall. Right on the cusp between '70s decadence and '80s preppiness, the casually thrown-together but tasteful look of this period is so smug yet all too attractive.
After Hours (1985)
Martin Scorsese captures, in a nutshell, the kooky downtown SoHo styles around the mid-'80s. Pretty Woman (1990)
This is a guilty pleasure -- a lot like fashion.
Gia (1998)
A supermodel junkie tragedy is neither glamorous nor inspiring, but Angelina Jolie is fabulous.
In The Mood For Love (2000)
Maggie Cheung must've worn about 200 different variations of the cheongsam dress in this movie and every single one is a knockout. Wong Kar-Wai has a way with colors in the grander scheme of things... a brilliant cinematographer!
Yves Saint-Laurent: 5 Avenue Marceau, 75116 Paris (2002)
In the opening scene, Saint-Laurent's life-long muse Catherine Deneuve stands in front of the mirror at 5 Avenue Marceau and repeats "Trés jolis, trés jolis." She's trying on one of the latest pieces by the designer, of course. It's such a touching moment.
Imelda (2003)
Beyond the shoes, you get Imelda's philosophies on beauty and politics. Even though she's a delusional has-been beauty queen, it's hard not to get a little smitten with this world's most notorious fashion victim.