Skip to content

Top Navigation

EW.com EW.com
    • All TV
    • TV Reviews
    • TV Reunions
    • Recaps
    • What to Watch
    • Winter TV
    • Comedy
    • Crime
    • Drama
    • Family
    • Horror
    • Reality
    • Sci-fi
    • Thriller
    • All Movies
    • Movie Reviews
    • Trailers
    • Film Festivals
    • Movie Reunions
    • Movie Previews
    • All Music
    • Music Reviews
    • All What to Watch
    • What to Watch Podcast Episodes
    • TV Reviews
    • Movie Reviews
    • All BINGE
    • EW's Binge Podcast Episodes
    • Recaps
    • Survivor
    • This is Us
    • RuPaul's Drag Race
    • Stranger Things
    • The Boys
    • The Blacklist
    • The Walking Dead
    • Better Call Saul
    • All The Awardist
    • The Awardist Podcast Episodes
    • Oscars
    • Emmys
    • Golden Globes
    • SAG Awards
    • Grammys
    • Tony Awards
    • All Books
    • Book Reviews
    • Author Interviews
    • All Theater
    • Theater Reviews
  • Podcasts
  • Gaming
    • All Events
    • Comic-Con
  • Celebrity
  • Streaming

Profile Menu

Your Profile

Account

  • Join Now
  • Email Preferences
  • Newsletter
  • Manage Your Subscription this link opens in a new tab
  • Give a Gift Subscription this link opens in a new tab
  • Logout
Login
Subscribe

Explore EW.com

EW.com EW.com
  • Explore

    Explore

    • The 10 best songs of 2022

      The 10 best songs of 2022

      From disco-trap to deconstructed techno to Dolly-style country, we rank our favorite tracks this year. Read More
    • The 10 best movies of 2022 (and 5 worst)

      The 10 best movies of 2022 (and 5 worst)

      Let there be Mavericks, Bollywood magic, and a Cate Blanchett maestro on the loose. Read More
    • The true story of the g-strings and murders behind Welcome to Chippendales

      The true story of the g-strings and murders behind Welcome to Chippendales

      A look back at the crazy true story of Chippendales founder Somen "Steve" Banerjee and the murder and murder-for-hire plots at the center of the Hulu series. Read More
  • TV

    TV

    See All TV
    • TV Reviews
    • TV Reunions
    • Recaps
    • What to Watch
    • Winter TV
    • Comedy
    • Crime
    • Drama
    • Family
    • Horror
    • Reality
    • Sci-fi
    • Thriller
  • Movies

    Movies

    See All Movies
    • Movie Reviews
    • Trailers
    • Film Festivals
    • Movie Reunions
    • Movie Previews
  • Music

    Music

    See All Music
    • Music Reviews
  • What to Watch

    What to Watch

    See All What to Watch
    • What to Watch Podcast Episodes
    • TV Reviews
    • Movie Reviews
  • BINGE

    BINGE

    See All BINGE
    • EW's Binge Podcast Episodes
    • Recaps
    • Survivor
    • This is Us
    • RuPaul's Drag Race
    • Stranger Things
    • The Boys
    • The Blacklist
    • The Walking Dead
    • Better Call Saul
  • The Awardist

    The Awardist

    See All The Awardist
    • The Awardist Podcast Episodes
    • Oscars
    • Emmys
    • Golden Globes
    • SAG Awards
    • Grammys
    • Tony Awards
  • Books

    Books

    See All Books
    • Book Reviews
    • Author Interviews
  • Theater

    Theater

    See All Theater
    • Theater Reviews
  • Podcasts
  • Gaming
  • Events

    Events

    See All Events
    • Comic-Con
  • Celebrity
  • Streaming

Profile Menu

Subscribe this link opens in a new tab
Your Profile

Account

  • Join Now
  • Email Preferences
  • Newsletter
  • Manage Your Subscription this link opens in a new tab
  • Give a Gift Subscription this link opens in a new tab
  • Logout
Login
Sweepstakes

Follow Us

  1. Home
  2. Gallery
  3. 25 Fashion Moments That Changed Entertainment

25 Fashion Moments That Changed Entertainment

By EW Staff February 18, 2016 at 04:38 PM EST
Skip gallery slides
FB

1 of 26

FB
Tweet Pinterest Email Send Text Message

Entertainment's Biggest Fashion Moments

Entertainment's Biggest Fashion Moments
Credit: Vinnie Zuffante/Getty Images; Tim Roney/Getty Images; NBC/NBCU Photo Bank via Getty Images; Dave Hogan/Getty Images; HBO

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.

 

1 of 26

Advertisement
Advertisement

2 of 26

FB
Tweet Pinterest Email Send Text Message

25. The 90210 'Burns, 1990

25. The 90210 'Burns, 1990
Credit: Fox

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.

 

2 of 26

3 of 26

FB
Tweet Pinterest Email Send Text Message

24. Ashton’s Trucker Hats, 2003

24. Ashton’s Trucker Hats, 2003
Credit: Steve Granitz Archive/WireImage

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

 

3 of 26

Advertisement
Continued on next slide.
Advertisement

4 of 26

FB
Tweet Pinterest Email Send Text Message

23. Seth Cohen’s Geek Chic, 2003

23. Seth Cohen’s Geek Chic, 2003
Credit: Glenn Watson/Warner Bros./Getty Images)

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

 

4 of 26

Advertisement

5 of 26

FB
Tweet Pinterest Email Send Text Message

22. Shania’s Midriff, 1995

22. Shania’s Midriff, 1995
Credit: Evan Agostini/Liaison

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

 

5 of 26

6 of 26

FB
Tweet Pinterest Email Send Text Message

21. Maddox’s Fauxhawk, 2004

21. Maddox’s Fauxhawk, 2004
Credit: Pascal Le Segretain/Getty Images

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.

 

6 of 26

Advertisement
Advertisement
Continued on next slide.
Advertisement

7 of 26

FB
Tweet Pinterest Email Send Text Message

20. Rihanna, 2007

20. Rihanna, 2007
Credit: Jeff Kravitz/FilmMagic

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.

 

7 of 26

Advertisement
Advertisement

8 of 26

FB
Tweet Pinterest Email Send Text Message

19. The Strokes, 2001

19. The Strokes, 2001
Credit: Anthony PIdgeon/Redferns

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

 

8 of 26

Advertisement

9 of 26

FB
Tweet Pinterest Email Send Text Message

18. George Clooney’s Caesar

18. George Clooney’s Caesar
Credit: Sven Arnstein/NBCU Photo Bank

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.

 

9 of 26

Advertisement
Advertisement
Continued on next slide.
Advertisement

10 of 26

FB
Tweet Pinterest Email Send Text Message

17. Kanye West, 2007

17. Kanye West, 2007
Credit: Dave Hogan/Getty Images

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

 

10 of 26

Advertisement
Advertisement
Advertisement

11 of 26

FB
Tweet Pinterest Email Send Text Message

16. Gwen Stefani, 1996

16. Gwen Stefani, 1996
Credit: Tim Mosenfelder/Getty Images

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

 

11 of 26

Advertisement
Advertisement

12 of 26

FB
Tweet Pinterest Email Send Text Message

15. André 3000, “Hey Ya!” 2003

15. André 3000, “Hey Ya!” 2003
Credit: Kevin Winter/Getty Images

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

 

12 of 26

Advertisement
Advertisement
Continued on next slide.
Advertisement

13 of 26

FB
Tweet Pinterest Email Send Text Message

14. Fiona Apple, 1997

14. Fiona Apple, 1997

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

 

13 of 26

Advertisement
Advertisement
Advertisement

14 of 26

FB
Tweet Pinterest Email Send Text Message

13. Marky Mark’s Underwear, 1991

13. Marky Mark’s Underwear, 1991
Credit: Tim Roney/Getty Images

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

 

14 of 26

Advertisement
Advertisement

15 of 26

FB
Tweet Pinterest Email Send Text Message

12. The Matrix, 1999

12. The Matrix, 1999
Credit: Jasin Boland

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

 

15 of 26

Advertisement
Advertisement
Continued on next slide.
Advertisement

16 of 26

FB
Tweet Pinterest Email Send Text Message

11. Clueless, 1995

11. Clueless, 1995
Credit: Elliott Marks

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

 

16 of 26

Advertisement
Advertisement
Advertisement

17 of 26

FB
Tweet Pinterest Email Send Text Message

10. Courtney Love, 1995

10. Courtney Love, 1995
Credit: Mick Hutson/Redferns

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 of 26

Advertisement
Advertisement

18 of 26

FB
Tweet Pinterest Email Send Text Message

9. “Mo Money Mo Problems," 1997

9. “Mo Money Mo Problems," 1997

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

 

18 of 26

Advertisement
Advertisement
Continued on next slide.
Advertisement

19 of 26

FB
Tweet Pinterest Email Send Text Message

8. Ally McBeal’s Skirts, 1997

8. Ally McBeal’s Skirts, 1997
Credit: Everett Collection

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.

 

19 of 26

Advertisement
Advertisement
Advertisement

20 of 26

FB
Tweet Pinterest Email Send Text Message

7. Britney Spears, 1998:

1999: The “...Baby One More Time” Music Video

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.

 

20 of 26

Advertisement
Advertisement

21 of 26

FB
Tweet Pinterest Email Send Text Message

6. The Rachel, 1995

6. The Rachel, 1995
Credit: NBC/NBCU Photo Bank

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.

 

21 of 26

Advertisement
Advertisement
Continued on next slide.
Advertisement

22 of 26

FB
Tweet Pinterest Email Send Text Message

5. The Best and Worst Red Carpet Outfits, 2000 and 2001

5. The Best and Worst Red Carpet Outfits, 2000 and 2001
Credit: Scott Gries/ImageDirect via Getty Images; Vinnie Zuffante/Getty Images

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.

 

22 of 26

Advertisement
Advertisement
Advertisement

23 of 26

FB
Tweet Pinterest Email Send Text Message

4. Amy Winehouse, 2007

4. Amy Winehouse, 2007
Credit: Roger Kisby/Getty Images

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

 

23 of 26

Advertisement
Advertisement

24 of 26

FB
Tweet Pinterest Email Send Text Message

3. Kurt Cobain, 1991

3. Kurt Cobain, 1991
Credit: Kevin Mazur Archive/WireImage

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

 

24 of 26

Advertisement
Advertisement
Continued on next slide.
Advertisement

25 of 26

FB
Tweet Pinterest Email Send Text Message

2. Sharon Stone at the Oscars, 1996

2. Sharon Stone at the Oscars, 1996
Credit: Michael Owen Baker/Los Angeles Daily News/AP

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

 

25 of 26

Advertisement
Advertisement
Advertisement

26 of 26

FB
Tweet Pinterest Email Send Text Message

1. The Opening Credits of Sex and the City, 1998

1. The Opening Credits of Sex and the City, 1998
Credit: HBO

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.

 

26 of 26

Advertisement
Advertisement
Replay gallery

Share the Gallery

Pinterest Facebook

Up Next

By EW Staff

    Share the Gallery

    Pinterest Facebook
    Trending Videos
    Advertisement
    Skip slide summaries

    Everything in This Slideshow

    Advertisement

    View All

    1 of 26 Entertainment's Biggest Fashion Moments
    2 of 26 25. The 90210 'Burns, 1990
    3 of 26 24. Ashton’s Trucker Hats, 2003
    4 of 26 23. Seth Cohen’s Geek Chic, 2003
    5 of 26 22. Shania’s Midriff, 1995
    6 of 26 21. Maddox’s Fauxhawk, 2004
    7 of 26 20. Rihanna, 2007
    8 of 26 19. The Strokes, 2001
    9 of 26 18. George Clooney’s Caesar
    10 of 26 17. Kanye West, 2007
    11 of 26 16. Gwen Stefani, 1996
    12 of 26 15. André 3000, “Hey Ya!” 2003
    13 of 26 14. Fiona Apple, 1997
    14 of 26 13. Marky Mark’s Underwear, 1991
    15 of 26 12. The Matrix, 1999
    16 of 26 11. Clueless, 1995
    17 of 26 10. Courtney Love, 1995
    18 of 26 9. “Mo Money Mo Problems," 1997
    19 of 26 8. Ally McBeal’s Skirts, 1997
    20 of 26 7. Britney Spears, 1998:
    21 of 26 6. The Rachel, 1995
    22 of 26 5. The Best and Worst Red Carpet Outfits, 2000 and 2001
    23 of 26 4. Amy Winehouse, 2007
    24 of 26 3. Kurt Cobain, 1991
    25 of 26 2. Sharon Stone at the Oscars, 1996
    26 of 26 1. The Opening Credits of Sex and the City, 1998

    Share & More

    Tweet Pinterest Email Send Text Message
    EW.com

    Magazines & More

    Learn More

    • Subscribe this link opens in a new tab
    • Advertise this link opens in a new tab
    • Content Licensing this link opens in a new tab
    • Accolades this link opens in a new tab

    Connect

    Subscribe to Our Newsletter
    Meredith© Copyright 2023 Meredith Corporation. Entertainment Weekly is a registered trademark of Meredith Corporation All Rights Reserved. Entertainment Weekly may receive compensation for some links to products and services on this website. Offers may be subject to change without notice. Privacy Policythis link opens in a new tab Terms of Servicethis link opens in a new tab Ad Choicesthis link opens in a new tab California Do Not Sellthis link opens a modal window Web Accessibilitythis link opens in a new tab
    © Copyright EW.com. All rights reserved. Printed from https://ew.com

    View image

    25 Fashion Moments That Changed Entertainment
    this link is to an external site that may or may not meet accessibility guidelines.