25 Fashion Moments That Changed Entertainment

From glitter and grunge to haircuts copied 'round the world, check out pop culture's coolest style hits, ahead.

Want more? EW has detailed the best in movies, TV, music, and books for 25 years with the Must List, and in celebration, The Must List: Ranking the Best in 25 Years of Pop Culture is out now. This gallery is an excerpt from the book. The Must List: Ranking the Best in 25 Years of Pop Culture is in stores now, or available for order online.

Now everyone knows size matters... when it comes to sideburns. The first TV teen drama of the '90s gave teen mags a new crop of cover boys and increased sideburn length by 56 percent.

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

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

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

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.

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.

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

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.

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

The ska-popster took SoCal street style to the suburbs, popularizing white tanks, studded bra straps, bondage pants, and trackies.

The dapper rapper brought body-conscious cuts and quality fabrics to hip-hop’s baggier street style.

The “Criminal” waif co-opted CK’s voyeuristic ads to sell... herself — and slippy, strappy tanks — to fans everywhere.

AKA the waistband that ignited a revolution. The peekaboo underwear was easy to emulate. The abs, not so much.

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

Teenagers in designer wares talking endlessly on their cell phones? At the time, it played like an over-the-top parody. Today — oh, whatever.

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.

In their coordinated leisure wear, Puff Daddy and Mase elevated bright, baggy tracksuits to hip-hop couture.

The hardworking but flighty lawyer (Calista Flockhart) and her much-debated micro minis made the workplace a safe haven for women’s bare legs everywhere.

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.

There was no haircut more desired in the Clinton era than the layered shag sported by waitress Rachel Green (Jennifer Aniston) on Friends. Twenty years later, Aniston calls it "the ugliest haircut" she’s ever seen.

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 Bjork’s choice of avian apparel at the 2001 Oscars made the Icelandic singer a household name — and a lifelong sartorial punchline.

A sweet tart in teeny frocks, bold bras, and sky-high bouffant, the British singer was embraced by high fashion.

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

When the outlandish actress paired Armani and Valentino with a Gap mock turtleneck, she kick-started the high-low fashion phenom.

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 — or blame.