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The 50 Pop Culture Moments That Rocked Fashion

The New Classics: Style -- From Amy Winehouse's hair to Marky Mark's tighty whities, a rundown of the highs and lows of celebrity looks

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1 Madonna at the MTV Video Music Awards (1984)
Like a virgin? Not quite. When the burgeoning pop singer formerly known as Ms. Ciccone hit the stage in a lingerie-like wedding dress, fingerless gloves, and multiple crucifixes — the first of many signature looks — a star was born. Her bold tweaking of sexual mores may seem commonplace now, but to a nation of young women, it was a revelation.

2 The Opening Credits of Sex and the City (1998)
The tutu was just the beginning; Carrie Bradshaw (Sarah Jessica Parker) became the tastemaker who kept on giving. So the next time you wear stilettos to walk the dog, you know who to thank.

3 Michael Jackson in ''Thriller'' (1983)
From the Jheri curl and loafers with white socks to the red leather jacket, MJ had a generation dressing — and moonwalking — to his beat.

4 Sharon Stone at the Oscars (1996)
When the outlandish actress paired Armani and Valentino with a Gap mock turtleneck, she kick-started the hi-lo fashion phenom.

5 Kurt Cobain (1991)
The Nirvana frontman became the reluctant king of grunge, inspiring a league of acolytes clad in grandpa cardigans, Converse kicks, and lumberjack plaid.

6 Mr. T in The A-Team (1983)
Some may credit Lil Wayne with coining bling for boys, but it was this original tough guy who, as Sgt. B.A. Baracus, pitied the fool who didn't have 20 pounds of gold chains. (The geometric haircut and big guns were pure bonus.)

7 Amy Winehouse (2007)
A sweet tart in teeny frocks, bold bras, and sky-high bouffant, the British singer was embraced by high fashion even as her personal life — and hygiene — went south.

8 & 9 The Best & the Worst
These days, stars are created on the red carpet just as much as they are on screen. Jennifer Lopez introduced her assets to the world at the 2000 Grammys in a plunging Versace, while Björk's choice of avian apparel at the 2001 Oscars made the Icelandic singer a household name — and a lifelong sartorial punchline.

10 The Rachel (1994)
There was no haircut more desired in the Clinton era than the layered shag sported by waitress Rachel Green (Jennifer Aniston) on Friends.

11 Britney Spears (1998)
Playing a sexy schoolgirl in ''...Baby One More Time'' worked music-chart magic for Spears — and set the standard by which all Lolita pop stars are judged.

12 Ally McBeal's Skirts (1997)
The flighty lawyer (Calista Flockhart) and her much-debated microminis made the workplace a safe haven for women's bare legs.

13 Risky Business (1983)
Sure, Tom Cruise was great. But the real takeaway? Ray-Bans and tighty whities make for hot accessories.

14 ''Mo Money Mo Problems'' (1997)
In their coordinated leisure wear, Puff Daddy and Mase elevated bright, baggy tracksuits to hip-hop couture.

15 Clueless (1995)
Teenagers in designer wares talking on their cell phones all day? At the time, it played like an over-the-top parody. Today, it — oh, whatever.

16 Courtney Love (1995)
The lead singer of Hole stole the crown (or, actually, the tiara) from Aqua Netted beauty queens. She appropriated vintage slip dresses, Mary Janes, and home-grown dye jobs, too. Some said the look played with traditional female stereotypes; others argued it mocked all things girly. The rest of us just thought she rocked.

17 The Matrix (1999)
How many leather trenches and Neo-style shades were misguidedly purchased to capture the sleek, futuristic allure of the hit movie? Too many, friends.

18 Pretty Woman(1990)
The romantic comedy put Julia Roberts and Rodeo Drive on the map with the Best Shopping Montage Ever.

19 Janet Jackson (1989)
Miss Janet adapted her brother's crisp military look for the ladies — with epaulets, cadet caps, fierce tailoring — in ''Rhythm Nation.''

20 Marky Mark's Underwear (1991)
A.k.a. the waistband that ignited a revolution. The peekaboo underwear was easy to emulate. The abs, not so much.

21 Bruce Springsteen (1984)
Forget apple pie — the Boss made a white shirt and blue jeans as American as it gets when dancing in the dark.

22 Fiona Apple (1997)
The ''Criminal'' waif co-opted CK's voyeuristic ads to sell...herself — and slippy, strappy tanks — to fans everywhere.

23 André 3000, ''Hey Ya!'' (2003)
The dapper rapper brought body-conscious cuts and quality fabrics to hip-hop's baggier street style.

24 Flashdance (1983)
After seeing Jennifer Beals' star turn, a generation of girls busted out their sweatshirts and a pair of scissors.

25 Gwen Stefani (1996)
The ska-popster took SoCal street style to the suburbs, popularizing white tanks, studded bra straps, bondage pants, and trackies.

26 Kanye West (2007)
A dedicated follower of both luxury brands and avant-garde outsiders, West inspired a thousand admirers in odd sunglasses.

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.

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.

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.

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.

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?)

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.

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.

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.

35 The Strokes (2001)
Why are entire cities filled with hipsters wearing blazers, rocker tees, and skinny jeans? Blame this band.

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.

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.

38 Maddox's Fauxhawk (2004)
When the little guy surfaced at mom Angelina's premiere with a spiky blue 'do, he set off a trend of adult-size 'hawks — and designer babies.

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.

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.

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.

42 Urkel (1989)
Family Matters lead dweeb (Jaleel White) finally gave high-waisted pants the bad name they deserved.

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.

44 Boy George (1983)
Boys in need of eyeliner tips were forever indebted to the gender-tweaking chameleon.

45 & 46 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.

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.

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.

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?

50 The 90210 'Burns (1990)
Now everyone knows size matters...when it comes to sideburns.

— Meeta Agrawal, Leah Greenblatt, Tim Stack