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21 Times Drew Barrymore Killed The Whole Fashion Thing In The ’90s

She literally personified the 1990s.

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1. The time she looked effortlessly cool and sexy while wearing men's clothing:

And giving Marky Mark a run for his money by proudly showing off her Calvin Klein underwear.
WireImage Steve.Granitz

And giving Marky Mark a run for his money by proudly showing off her Calvin Klein underwear.

2. The time she channeled Cher Horowitz by wearing a satin empire-waist dress and patent leather shoes:

Basically, the LOOK circa 1995.
WireImage/ Ron Galella

Basically, the LOOK circa 1995.

3. The time she looked Delia's-catalog cool in her skater-inspired outfit:

WireImage/ Jim Smeal

4. The time she brought vampy glamour to the 1995 VMAs:

Eat your heart out, Vampira!
WireImage/ Ron Galella, Ltd.

Eat your heart out, Vampira!

5. The time she accessorized her look with an oh-so-trendy choker:

WireImage/ Jim Smeal

6. The time she managed to still look chic while wearing baggy clothes:

The LIFE Picture Collection / Getty Time Life Pictures

7. The time she made the whole vest look work:

WireImage/ Ron Galella

8. The time she looked awesome in the late '90s sheer top trend:

WireImage/ Ron Galella

9. The time she looked fierce while wearing a velvet cheetah-print coat:

WireImage/ Ron Galella, Ltd.

10. The time she walked the fine line between feminine and grungy:

And pulled it off perfectly!
WireImage/ Ron Galella

And pulled it off perfectly!

11. The time she looked polished in her 1940s-inspired outfit:

WireImage/ Jim Smeal

12. The time she rocked the shit out of the little black (satin, of course) dress:

Also, what the hell is Sharon Stone wearing? Did she come straight from the gym to the red carpet?
WireImage/ Ron Galella, Ltd.

Also, what the hell is Sharon Stone wearing? Did she come straight from the gym to the red carpet?

13. The time she looked flawless in every late '90s girl's dream prom dress:

WireImage/ Ron Galella, Ltd.

14. The time she did the whole boho thing before it even existed:

WireImage/ Steve.Granitz

15. The time she looked badass even while wearing a polka dot and rose printed blouse:

WireImage/ Jim Smeal

16. The time she showed up to the Reservoir Dogs premiere wearing Daisy Dukes:

Accessorized with a pack of Camels.
WireImage/ Steve.Granitz

Accessorized with a pack of Camels.

17. The time she totally owned secretary style:

NY Daily News via Getty Images/ New York Daily News Archive

18. The time she showed up to the Batman Forever premiere wearing two thrift store slip dresses:

WireImage/ Steve.Granitz

19. The time she brought out her inner hippie child by wearing flowers in her hair to the Oscars.

WireImage/ Steve.Granitz

20. The time she rocked some serious black patent platforms:

Getty Images/ Martin Godwin

21. And finally, the time she epitomized '90s style by wearing a vest, cutoffs, and a seriously awesome fanny pack:

WireImage/ Jim Smeal

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