50 Stars Who Rocked Fashion: No. 50-26

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50. The 90210 'Burns (1990)

Everett Collection

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

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49. Ashton's Trucker Hats (2003)

Steve Granitz/WireImage

Could the Punk’d maestro’s biggest prank have been getting legions of hipsters to adopt the mesh-and-foam chapeaus of their fathers?

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48. The Cure (1987)

Simon Fowler/LFI

Brit singer Robert Smith’s goth look — in all of its inky-haired, bat-cave glory — begat another outlet for the behind-the-bleachers set.

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47. Seth Cohen's Geek Chic (2003)

The O.C: Fox

Ushering in the age of the Penguin-attired nerd, Adam Brody turned his dorky alter ego into The O.C.‘s unexpected cool kid.

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46. and 45. Mall Pop (1987)

Paul Natkin/WireImage; Lynn Goldsmith/Corbis

Pop princesses Debbie Gibson and Tiffany were the faces of electric youth in the ’80s — and their suburban Valley Girl ensembles became a look coveted by even the most soigné teens. Today, bike shorts, skorts, and scrunchies are considered crimes against humanity.

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44. Boy George (1983)

Ron Wolfson/WireImage

Boys in need of eyeliner tips were forever indebted to the gender-tweaking chameleon.

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43. Shania's Midriff (1995)

Nashville roared with disapproval at the sight of the crooner’s bare belly — until Twain topped the charts. Now sultry country honeys abound.

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42. Urkel (1989)

Everett Collection

Family Matters‘ lead dweeb (Jaleel White) finally gave high-waisted pants the bad name they deserved.

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41. Head of the Class (1986)

Resident rich girl Darlene (Robin Givens) attended Class in oversize blazers and tapered jeans that would become the preppy uniform of the ’80s.

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40. Reality Bites (1994)

Kobal Collection/WireImage.com

The slacker chic worn by the cult movie’s cast (as well as Lisa ”Stay” Loeb’s signature cat-eye frames) gave twentysomethings a new wardrobe for the coffee shop.

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39. Punky Brewster (1984)

Gary Null/AP

Like a T.G.I. Friday’s Employee of the Month, she loved her flair, and got others to embrace the many colors of the rainbow.

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38. Maddox's Fauxhawk (2004)

Domenico Stinellis/AP

When the little guy surfaced at mom Angelina’s Shark Tale premiere with a spiky blue ‘do, he set off a trend of adult-size ‘hawks — and designer babies.

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37. Gordon Gekko (1987)

Everett Collection

Slicked-back hair, shiny suits, and arrogance as his cologne of choice: The Wall Street tycoon (Michael Douglas) defined high-finance fashion.

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36. The Golden Girls (1985)

Kobal Collection/WireImage

The ladies of the lanai brought back three big S’s for the geriatric set. That would be sex, shoulder pads, and sequins, FYI.

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35. The Strokes (2001)

Sebastian Mlynarski/Getty Images

Why are entire cities filled with hipsters wearing blazers, rocker tees, and skinny jeans? Blame this band.

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34. Salt-N-Pepa (1987)

Janette Beckman/Retna

Until S-N-P (and Spinderella!) came on the scene, rap was mostly a boys’ club. But the ”Push It” singers feminized the genre by embracing sexuality in both their lyrics and their wardrobes.

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33. Rihanna (2007)

Mark J. Terrill/AP Photo

Many an R&B diva has taken on big-name fashion before, but none with the saucy punk-rock spirit of the Barbados-born songstress. She started out demure, but in chopping her locks she carved out her own identity — and a bob that was widely copied, as would be her many other subsequent incarnations.

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32. Axl Rose (1987)

Jeffrey Mayer/WireImage

The Guns N’ Roses frontman’s dirty-sexy glamour was easy to imitate: Take a pair of holey jeans, add a bandanna, and pile on the hair.

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31. Pretty in Pink (1986)

Everett Collection

Teens swooned over Molly Ringwald’s DIY reconstructed prom dress. Well, that and her singularly styled date, Duckie. (Who else could pull off the bolo tie?)

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30. G.I. Jane (1997)

Everett Collection

When Demi Moore went from sexy Stripteaser to hard-bodied, head-shaved SEAL, women flocked to the gym — though, thankfully, not to the barber.

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29. A Different World (1987)

Deborah Feingold/Corbis

Cosby Show cutie Denise Huxtable (Lisa Bonet) graduated to a spin-off, and the boho-bourgie styles of the Hillman College campus.

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28. George's Caesar (1995)

Rene Macura/AP

When Dr. Doug Ross cut his curly locks on ER, he sparked a hair craze for the male masses — and rolled out Clooney 2.0, debonair movie star.

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27. Miami Vice (1984)

Everett Collection

Never before — or, likely, again — would so many men don roomy linen suits and sockless loafers in an effort to emulate the pastel-tinged cool of TV’s hippest cop duo.

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26. Kanye West (2007)

Kevin Winter/Getty Images

A dedicated follower of both luxury brands and avant-garde outsiders, West inspired a thousand admirers in odd sunglasses.

Replay gallery

Account

50 Stars Who Rocked Fashion: No. 50-26

1 of 25

50. The 90210 'Burns (1990)

1 of 25

2 of 25

49. Ashton's Trucker Hats (2003)

2 of 25

3 of 25

48. The Cure (1987)

3 of 25

4 of 25

47. Seth Cohen's Geek Chic (2003)

4 of 25

5 of 25

46. and 45. Mall Pop (1987)

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6 of 25

44. Boy George (1983)

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7 of 25

43. Shania's Midriff (1995)

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8 of 25

42. Urkel (1989)

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9 of 25

41. Head of the Class (1986)

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10 of 25

40. Reality Bites (1994)

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11 of 25

39. Punky Brewster (1984)

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38. Maddox's Fauxhawk (2004)

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37. Gordon Gekko (1987)

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36. The Golden Girls (1985)

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35. The Strokes (2001)

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34. Salt-N-Pepa (1987)

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33. Rihanna (2007)

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32. Axl Rose (1987)

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31. Pretty in Pink (1986)

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30. G.I. Jane (1997)

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29. A Different World (1987)

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28. George's Caesar (1995)

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27. Miami Vice (1984)

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26. Kanye West (2007)

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