The 90210 ‘Burns, 1990

Now everyone knows size matters… when it comes to sideburns.

Now sultry country honeys abound.

Andre 3000, Hey Ya!

Entertainment’s Biggest Fashion Moments

Vinnie Zuffante/Getty Images; Tim Roney/Getty Images; NBC/NBCU Photo Bank via Getty Images; Dave Hogan/Getty Images; HBO

2003

The dapper rapper brought body-conscious cuts and quality fabrics to hip-hops baggier street style.

Marky Marks Underwear, 1991

AKA the waistband that ignited a revolution.

The peekaboo underwear was easy to emulate.

25. The 90210 ‘Burns, 1990

Fox

The abs, not so much.

Too many, friends.

Clueless, 1995

Teenagers in designer wares talking endlessly on their cell phones?

24. Ashton’s Trucker Hats, 2003

Steve Granitz Archive/WireImage

At the time, it played like an over-the-top parody.

Today oh, whatever.

She appropriated vintage slip dresses, Mary Janes, and home-grown dye jobs, too.

23. Seth Cohen’s Geek Chic, 2003

Glenn Watson/Warner Bros./Getty Images)

Some said the look played with traditional female stereotypes; others argued it mocked all things girly.

The rest of us just thought she rocked.

Twenty years later,Aniston calls it"the ugliest haircut" shes ever seen.

22. Shania’s Midriff, 1995

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So the next time you wear stilettos to walk the dog, you know who to thank or blame.

21. Maddox’s Fauxhawk, 2004

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20. Rihanna, 2007

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19. The Strokes, 2001

Anthony PIdgeon/Redferns

18. George Clooney’s Caesar

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17. Kanye West, 2007

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16. Gwen Stefani, 1996

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15. André 3000, “Hey Ya!” 2003

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14. Fiona Apple, 1997

13. Marky Mark’s Underwear, 1991

Tim Roney/Getty Images

12. The Matrix, 1999

Jasin Boland

11. Clueless, 1995

Elliott Marks

10. Courtney Love, 1995

Mick Hutson/Redferns

9. “Mo Money Mo Problems," 1997

8. Ally McBeal’s Skirts, 1997

Everett Collection

1999: The “…Baby One More Time” Music Video

6. The Rachel, 1995

NBC/NBCU Photo Bank

5. The Best and Worst Red Carpet Outfits, 2000 and 2001

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4. Amy Winehouse, 2007

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3. Kurt Cobain, 1991

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2. Sharon Stone at the Oscars, 1996

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1. The Opening Credits of Sex and the City, 1998

HBO