The Most Profoundly Regrettable Moments in 1990s Musical Fashion


With the inevitable 1990s revival in full swing these days, it’s perhaps a good time to remind ourselves that it can be awfully easy to look back at the past with distinctly rose-colored glasses. Sure, the ’90s gave rise to some definitive musical trends, the influence of which is still felt today — the tail end of acid house, the advent of grunge, the evolution of hip hop into a full-fledged commercial behemoth. It also gave rise to some distinctive musical fashion, as anyone who sports a Cobain-esque flannelette shirt can attest. But lest we forget, much of the decade was also a pretty dark time for both music and musical fashion — so in a lighthearted spirit of reminiscence, here’s a look back at some of the most profoundly dreadful music-related fashion statements of the decade. What did we miss?

Vanilla Ice

Sure, there’s the jacket, the quiff, and the general air of self-satisfaction (which was presumably dispelled forever once Suge Knight dangled him out of a window). But the most disturbing thing here is… the semi-shaved eyebrow. What’s that all about?

Tupac Shakur

Speaking of Suge, here he is in trademark Bloods suit. But, um, how’s about those leather overalls that Tupac is sporting, then? Ride ’em, cowboy!


Tupac wasn’t the only guilty party in the 1990s overall department, mind. Here’s Justin Timberlake, clearly prior to bringing sexy back…

New Kids on the Block

… although at least Timberlake et al had the decency to wear something under their overalls. Eeek.

Right Said Fred

He’s too sexy for his shirt. Obviously.

MC Hammer

Think of the early ’90s, and it’s pretty much impossible not to think of Hammer pants. This single image is why MC Hammer never made it as a gangsta rapper, despite his late 1990s attempts to do exactly that.

Kriss Kross

… and along with Hammer pants, here’s the other defining image of silly early-’90s commercial hip hop fashion: two kids wearing their clothes backwards. It was a strange time for everyone.


Look, we don’t mean to be nasty here, since Hanson were about 12 when this was taken, but still: what on Earth is with that shirt?

Spin Doctors

Photographic proof: the single worst and most irritating band of the 1990s once graced the cover of Rolling Stone, decked out in their thrift shop finest for the big occasion. “Rock’s Road Warriors,” apparently. If you say so, Rolling Stone.

Pop Will Eat Itself

The “wacky hobo” look adopted by Spin Doctors may or may not have had its roots in grebo, the curious turn-of-the-’90s genre popularized in the UK in the wake of acid house. The preponderance of semi-shaved heads and dreadlocks only went to show that if you took enough drugs, anything seemed like a good idea.


And, speaking of dreadlocks, we’d be remiss not to mention Korn. In fairness to Jonathan Davis, he hasn’t abandoned his unique fashion sense — he still looks exactly like this, except for a receding hairline.


Well, Snow, here’s the thing: if you were wearing that shirt, we’d totally have informed on you, too.

Faith No More

For anyone who grew up after the 1990s, Mike Patton is a suave crooner who makes ultra-sleek records based on Italian film soundtracks and looks pretty awesome next to a classy old car. It was not always so.


Yes, that really is Prince’s ass. At least he has a good reason for owning such pants, though — he used to be a stripper, y’know.

Will Smith

Oh yes, Will Smith was profoundly irritating long before Independence Day/Men in Black/dynastic world domination. Nice hat, Fresh Prince!

Billy Ray Cyrus

Further proof that being a godawful “celebrity” is at least partly a genetic predisposition.


But it’s ironic! And a comment on consumerism! And… ah, fuck it, let’s just go and make All That You Can’t Leave Behind, shall we?


The dawn of the decade was a dark time for music generally, but particularly so for anything that involved guitars and distortion. Hair metal peaked in about 1990, and there were few more gloriously absurd bands than Warrant. All together now: “She’s my cherry pie…”

Mr. Big

At least Warrant were fun, though. The early 1990s also saw a preponderance of thoroughly soppy big-haired bands like Mr. Big, who rode a mixture of dire pseudo-metal aesthetics and soppy balladry to chart domination worldwide. See also: Extreme. Worse was to come, though…

Guns N’ Roses

There are no words, really.

Jeff Ament

Of course, grunge didn’t exactly shine in the fashion stakes either. Most bands kept things pretty low-key — all flannelette shirts and ripped jeans — but there was always Pearl Jam’s Jeff Ament to fly the flag for silly 1990s fashion. Bless him.

Spice Girls

Yeah, Girl Power! Vote Conservative! Wear ridiculous outfits! Pander to clichéd music industry conception of male fantasies! Make money hand over fist! You go, Spice Girls!

2 Unlimited

And, then, finally, the worst of the worst as far as ’90s musical and fashion trends go: Eurodance. The early and mid ’90s were full of bands who looked like this: Technotronic, Snap, Black Box…


… and Aqua. Good grief. Avert your eyes, kids.

Aqua, again

We warned you!