More from EW
1 of 24
25. Gwen Stefani (1996)
The ska-popster took SoCal street style to the suburbs, popularizing white tanks, studded bra straps, bondage pants, and trackies.
2 of 24
24. Flashdance (1983)
After seeing Jennifer Beals' star turn, a generation of girls busted out their sweatshirts and a pair of scissors.
3 of 24
23. André 3000, ''Hey Ya!'' (2003)
The dapper rapper brought body-conscious cuts and quality fabrics to hip-hop's baggier street style.
4 of 24
22. Fiona Apple (1997)
The ''Criminal'' waif co-opted CK's voyeuristic ads to sell...herself — and slippy, strappy tanks — to fans everywhere.
5 of 24
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.
6 of 24
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.
7 of 24
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.''
8 of 24
18. Pretty Woman (1990)
The romantic comedy put Julia Roberts and Rodeo Drive on the map with the Best Shopping Montage Ever.
9 of 24
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.
10 of 24
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.
11 of 24
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.
12 of 24
13 of 24
13. Risky Business (1983)
Sure, Tom Cruise was great. But the real takeaway? Ray-Bans and tighty whities make for hot accessories.
14 of 24
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.
15 of 24
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.
16 of 24
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.
17 of 24
9. and 8. 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.
18 of 24
7. Lady Gaga (2009)
Yes, Gaga had begun to make waves before 2009, but it was her grand entrance at the MTV Video Music Awards in a Jean Paul Gaultier lace dress with a neck brace by Keko of London that gave the world the first real inkling of the spectacle she'd present on- and offstage.
19 of 24
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.)
20 of 24
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.
21 of 24
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.
22 of 24
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.
23 of 24
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.
24 of 24
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.