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50. The 90210 'Burns (1990)
Now everyone knows size matters... when it comes to sideburns.
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49. Ashton's Trucker Hats (2003)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
A dedicated follower of both luxury brands and avant-garde outsiders, West inspired a thousand admirers in odd sunglasses.