Jennifer Lopez at the Grammys 2020

Top 10 Fashion Moments Of The Last 25 Years

Entertainment Weekly dedicated its latest issue to a survey of the finest moments in pop culture in the last 25 years, with scores of lists written to honor the best of current (well, recent) movies, songs, novels, TV shows, and so on. Of special interest to all of us in LatestBeauty Country, however, is the run-down of The 50 Pop Culture Moments That Rocked Fashion

EW Top 10 Fashion Moments Of The Last 25 Years

Read on for our overview of top 10 selections, as well as some of our options for pivotal fashion moments that didn’t make the final.

Madonna at the MTV Video Music Awards (1984)

Obviously, a massive moment, but it is, of course, uncertain if it is the most important of the last quarter of a century. Yet, Madonna has been both a sex symbol and a beauty trendsetter, and she’s still popular for both of them to this day. The It Element that distinguishes Madonna from other disposable pop tarts? She never seemed like a puppet; she really owned it. Brava, Madonna! You are now, as always, indisputably fierce.

The opening credits of ‘Sex and the City’ (1998)

Sarah Jessica Parker strutting boldly down the streets of Manhattan in a form-fitting leotard, blunt tutu, and trendy shoes like a 21st-century neo-ballerina created a bright new style model for women older than, say, 12 to imitate, filling a fashion vacuum that had been practically vacant for years in the teenybopper’s era. And when Carrie gets drenched with gutter water by a bus plastered with a huge ad for her own salacious sex column – well, women knew they had a heroine who was flawed, funny, and human in addition to being fabulous.

Michael Jackson in “Thriller” (1983)

Hearkening back to the days when Michael Jackson was indeed the King of Pop and not just a punchline, the “Thriller” video was fantastic for many reasons, not the least of which was how cool MJ looked in his red-and-black ensemble that bordered on nerd chic with its slightly-too-short pants and prominently featured white socks. Yes, children, there was a time when it seemed Michael Jackson could do no wrong: He was just a talented and, perhaps, ever so slightly eccentric dude. You could even buy him as a nice, average guy out on a date with his girlfriend. In retrospect, the end of an era.

Sharon Stone at the Oscars (1996)

The big news here was that Stone wore Armani, Valentino, and a short-sleeved turtleneck from the Gap (gasp!) to the Oscars, Hollywood’s most prestigious black-tie affair. Somewhat shockingly, people loved it, and the trend of embracing “low-end” clothing and mixing it with pricey couture was born. Enjoying the designer collections at Target, Payless, and H&M? In a roundabout way, you have Sharon Stone to thank!

Kurt Cobain (1991)

When Nirvana burst onto the mainstream rock scene with the “Smells Like Teen Spirit” video, an unwitting style icon was born in singer-songwriter-guitarist Kurt Cobain. He was so anti-fashion that it was fashionable. Kids everywhere stopped washing their hair and started wearing ripped jeans, cardigans, Converse, and flannel. It wasn’t long before Marc Jacobs was parading “grunge couture” down the runways, and the early ’90s slacker-chic aesthetic was everywhere.

Mr. T in ‘The A-Team’ (1983)

A bit of an odd choice, in my opinion – did people ever actually want to dress like Mr. T, or was he just affectionately chuckled at for his outlandish persona and loads of garish gold jewelry? – but here he is, nonetheless. EW credits him with starting the “bling for boys” trend (i.e., “I can wear sparkly jewelry and still be tough!”) that continues to flourish in the contemporary rap community, so maybe they’re on to something after all.

Amy Winehouse (2007)

Another strange pick for the top 10, since Amy, is such a recent phenomenon that it’s virtually impossible to say whether she’ll have any lasting impact, but she’s created such a sensation already that it would be remiss to leave her off altogether. Amy basically pioneered super-trashy-chic, from her incongruous beehive hairdo and crazy winged eyeliner to her prison tattoos and unapologetic appetite for drugs and alcohol. Again, I don’t know many people who want to look like her, but in a world where most modern pop stars are overly reliant on their stylists, she certainly stands out.

Jennifer Lopez at the Grammys (2000)

J.Lo solidified her celebrity status with this beyond-daring dress from Versace, which remains to this day the most notorious red carpet outfit of all time. Love it or hate it, you couldn’t ignore it.

Bjork at the Oscars (2001)

The same could certainly be said for Bjork’s bizarre swan dress (complete with egg-shaped purse, not pictured!) – only instead of making her a superstar. It seemed to lead most of the nation to conclude that the Icelandic singer was a certifiable nutjob. I think the Swan Incident was really misunderstood – if you’re familiar with Bjork’s music, which is also “out there,” it’s easy to see how her unique sensibilities probably led her to actually like this dress. Now, don’t get me wrong – I won’t be seeking out a replica to wear for myself anytime soon – but I don’t think Bjork meant it as a joke or a kiss-off to the Academy. But I digress. Here’s the issue: The woman wore a swan on the red carpet!

The Rachel (1994)

Simply put, the most significant haircut of the ’90s. Before she was a movie star, before she was Angelina’s Liz Taylor’s Debbie Reynolds in the most highly publicized love triangle of the new millennium, Jennifer Aniston had a little show called Buddies, and the boy had people like her hair.

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