1.
The time she looked effortlessly cool and sexy while wearing men's clothing:
2.
The time she channeled Cher Horowitz by wearing a satin empire-waist dress and patent leather shoes:
3.
The time she looked Delia's-catalog cool in her skater-inspired outfit:
4.
The time she brought vampy glamour to the 1995 VMAs:
5.
The time she accessorized her look with an oh-so-trendy choker:
6.
The time she managed to still look chic while wearing baggy clothes:
7.
The time she made the whole vest look work:
8.
The time she looked awesome in the late '90s sheer top trend:
9.
The time she looked fierce while wearing a velvet cheetah-print coat:
10.
The time she walked the fine line between feminine and grungy:
11.
The time she looked polished in her 1940s-inspired outfit:
12.
The time she rocked the shit out of the little black (satin, of course) dress:
13.
The time she looked flawless in every late '90s girl's dream prom dress:
14.
The time she did the whole boho thing before it even existed:
15.
The time she looked badass even while wearing a polka dot and rose printed blouse:
16.
The time she showed up to the Reservoir Dogs premiere wearing Daisy Dukes:
17.
The time she totally owned secretary style:
18.
The time she showed up to the Batman Forever premiere wearing two thrift store slip dresses:
19.
The time she brought out her inner hippie child by wearing flowers in her hair to the Oscars.
20.
The time she rocked some serious black patent platforms:
21.
And finally, the time she epitomized '90s style by wearing a vest, cutoffs, and a seriously awesome fanny pack:
