EW 1000: Style

50 Pop Culture Moments That Rocked Fashion

Madonna, ''Clueless,'' Ally McBeal's skirts, and more -- the standouts in pop-culture style since 1983


1. Madonna at the MTV Video Music Awards (1984)
2. Sarah Jessica Parker in the opening credits of Sex and the City (1998)
3. Michael Jackson in the ''Thriller'' video (1983)
4. Sharon Stone at the Oscars (1996)
5. Kurt Cobain and grunge style (1991)
6. Mr. T's gold chains in The A-Team (1983)
7. Amy Winehouse's frocks, bold bras, and sky-high bouffant (2007)
8. The best red carpet dress: Jennifer Lopez at the Grammys (2000)
9. The worst red carpet dress: Björk at the Oscars (2001)
10. Jennifer Aniston's haircut, The Rachel, on Friends (1994)
11. Britney Spears as a schoolgirl in ''...Baby One More Time'' (1998)
12. Calista Flockhart's skirts on Ally McBeal (1997)
13. Tom Cruise's Ray-Bans and tighty whities in Risky Business (1983)
14. Puff Daddy and Mase's bright tracksuits in ''Mo Money Mo Problems'' (1997)
15. Designer wares in Clueless (1995)
16. Courtney Love's vintage slip dresses, Mary Janes, and home-grown dye jobs (1995)
17. The leather trenches and Neo-style shades in The Matrix (1999)
18. Julia Roberts' Rodeo Drive shopping spree in Pretty Woman (1990)
19. Janet Jackson's military look in ''Rhythm Nation'' (1989)
20. Marky Mark's underwear(1991)
21. Bruce Springsteen's white shirt and blue jeans (1984)
22. Fiona Apple's strappy tanks (1997)
23. André 3000's baggy street look in ''Hey Ya!'' (2003)
24. Jennifer Beals' sweatshirts in Flashdance (1983)
25. Gwen Stefani's SoCal street style (1996)
26. Kanye West's sunglasses (2007)
27. Pastel-tinged linen suits and sockless loafers in Miami Vice (1984)
28. George Clooney's Caesar hairstyle on ER (1995)
29. Lisa Bonet's boho-bourgie style on A Different World (1987)
30. Demi Moore's shaved head in G.I. Jane (1997)
31. Molly Ringwald's prom dress in Pretty in Pink (1986)
32. Axl Rose's dirty-sexy glamour (1987)
33. Rihanna's hair bob (2007)
34. Salt-N-Pepa's sexy wardrobes (1987)
35. The Strokes' hipster look: blazers, rocker tees, and skinny jeans (2001)
36. The Golden Girls' shoulder pads and sequined tops (1985)
37. Michael Douglas' slicked hair and shiny suits as Gordon Gekko in Wall Street (1987)
38. Maddox's fauxhawk (2004)
39. Punky Brewster's colorful and flare-filled wardrobe (1984)
40. The slacker chic look in Reality Bites (1994)
41. Robin Givens' blazers and tapered jeans in Head of the Class (1986)
42. Jaleel White's high-waisted pants on Family Matters (1989)
43. Shania Twain's midriff (1995)
44. Boy George's eyeliner (1983)
45/46. Mall Pop: Debbie Gibson and Tiffany's suburban Valley Girl ensembles (1987)
47. Adam Brody's geek chic style on The O.C. (2003)
48. The goth look of Robert Smith and the Cure (1987)
49. Ashton Kutcher's trucker hats in Punk'd (2003)
50. The guys sporting sideburns in 90210 (1990)

Originally posted Jun 17, 2008 Published in issue #999-1000 Jun 27, 2008 Order article reprints
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