The 90 Greatest ’90s Fashion Trends

Image via Getty/Mitchell Gerber

So awesome—whether you rocked it with one strap or both straps down. Also, it had to be Guess, or else you were just playing yourself. And if you really wanted to be cool, you wore no shirt underneath—Jodeci style.

Ok, so you got a mood ring at the mall and sometimes you wore it just to see if maybe it actually worked. It didn't. And it looked dumb. But it was a good conversation starter and if you were lucky, it lead to a few steamy make-out sessions with the hot chick from homeroom.

Alien Workshop, Hook-Ups, Toy Machine, Thrasher, Spitfire, Girl—the explosion in popularity of street skating lead to mall rats all over America rocking graphic tees with skate logos. You don't see them as much anymore, now that the flannel and chinos uniform has taken hold.

Before skateboarding had its foothold in youth culture, in-line skating was a close competitor. At least half of us remember hanging out behind the mall "going aggro" in our K2s because that's how we rolled. And really, rocking a wristguard made you feel like a badass.

The two stripes from waist to ankle showed you had the cash flow of the rappers who rocked them at the time, but looking back, we were rocking tuxedo jeans. Lulz.

I keep one rolled up like LL's pant leg. - Curren$y. If you thought going to jail was cool, then you probably rocked this look. The trend definitely started on some gang shit, but LL Cool J made it appeal to the masses.

Hoop shorts were too short in the '90s, so guys started wearing these underneath. Then all of a sudden, fools were wearing bike shorts just on its own. Bam, new trend.

Teenagers everywhere know that in school, you're only as cool as the brands you wear. In the '90s, your denim had to be from Girbaud. Fancy fly required.

Thanks to INXS, the term "Suicide Blonde" was introduced into everyday conversation. And thanks to Guy Fieri, this trend lives on.

Pelle Pelle leathers were second to Avirex bombers. Still dope though.

These reached a pinnacle when they could be found in mall stores like The Gap—and they were made out of synthetic performance fabric like nylon... with cargo pockets... and a drawstring hem. That's the '90s if it were a pair of pants.

Back in the day, some people would stash their pot in the side pocket. But not us, other people.

If you know anything about West Coast rap, you would've had one of these caps in the '90s.

Perfect for showing how much of a badass you were, and also good for keeping track of where your shit was deep down in your long-ass jean pockets.

Forget the gym, wristbands were awesome for wearing to Warped Tour and hardcore shows. Bonus points if they had band names or video game characters on them.

Neon windbreakers were like magic capes. You threw one on and you were instantly the coolest guy in school. This trend was hot among every kind of kid, too. And the brighter, the better.

It's so sad how a brand's reputation can flip from awesome to not-so-awesome in a few years. Skechers, before their female friendly Shape-ups days, were popular with guys with their selection of skate shoes, Air Max 95-like trainers, and the half-dressy, half-sneaker hybrids.

Whether you were Kurt Cobain or Freddie Krueger, these were pretty prevalent in the era of grunge and Nightmare on Elm Street. If you ever wanted to destroy one, all you had to do was pull that thread, and walk away...

Tie one of these around your head and everyone knew which rapper you were aligning yourself with. (We're talking about Tupac for all you Juelz fans out there.) Funny thing is, bandannas were not only gang-related, they were gay-related, too. Look up the Handkerchief code if you're curious.

The chunky sole and heavily-labeled heel made BKs a go-to shoe choice for many young fans of hip-hop. The large tongue could have been a precursor the the moon-boot skate shoes the 90s would soon bring, and as an added bonus: British Knights proved popular amongst Crips gang members. We're willing to bet it wasn't because of MC Hammer's endorsement.

Because Nirvana didn't sound the same if you didn't have at least three holes in your denim.

Maybe it was Kurt Cobain. Or was it Axl Rose? Or Anthony Kiedis? Who knows who started it, but this trend took hold around the time that Headbangers Ball was on MTV, and white kids all across America stopped going to the barber so they could grow out their locks and swing their hair in the mosh pit.

Because deep down, every dude kind of had a thing for Daria Morgendorffer and Tank Girl.

Remember those zip hoodies with the "555-SOUL" embroidery? We used to wear that shit on the daily and re-up on the brand back when Yellow Rat Bastard was worth stepping into.

Super tech-y watches were all the rage these days, but G-Shocks were all that and a bag of chips. If you were a kid with one of these on your wrist, you were definitely PHAT.

Before Lil Wayne rocked ridic bottoms, rappers like Hammer and Vanilla Ice were all about wild pants. Hey—at least they weren't pajama jeans.

This was the de facto "cool guy" uniform of the '90s. Long-sleeve shirt, worn as a shirt jacket, with either a Nirvana or Daniel Johnston tee underneath. Perfect for seducing would-be riot grrrl posers and would-be indie kids.

Debuting in 1993 as an obvious competitor to Timberland, Lugz always had a connection to hip-hop. The thick soles and big boots were very in-style at the time and looked awesome with your sagged, baggy jeans, wife beater, and chain.

Made from a temperature-sensitive fabric that went from one color to another depending on the temperature, these T-shirts changed color when you touched them, resulting in a lot of handprints in inappropriate places. Washing them the wrong way also meant they got ruined.

This was how you dressed up in the '90s. You wore a baggy-ass suit, found a solid black crewneck T-shirt, and tucked it in. Think about the dude Christian in Clueless. This was his defacto outfit. Now think about where his career is and where the trend is. Yup.

In grade schools all over, the battle between Airwalks and Vans raged on for skate shoe supremacy. People were fiercely loyal to their brands, but in the end, Airwalks fell the fuck off and ended up at Payless.

No this ain't from the Disney store, this is from Daffy's, son.

A perfect example of how when somehow everyone likes something totally wack, it becomes cool. Reef Sandals are looked back on fondly while in the present day, we hate on Mark Zuckerburg for always rocking Adi Slides.

Supertight man tanks were all the rage on the bodies of stars like Jean-Claude Van Damme and Arnold Schwarzenegger. Being a big dude was favored in the '90s and what better way to show off the pecs and guns?

Started by then Rocafella affiliate Dame Dash, if you wanted to live like La Vida Roc, then you had to rock Rocawear.

If you hated the Discman because your favorite tracks would always skip, you at least enjoyed the stares you got from even having the $100+ player. The headphones became a status symbol, like having a gold tooth.

Name another place you could go to pick up a dope canvas backpack, bubble vest, down jacket, thermals, baggy jeans, and a kitted-out Ford Explorer. Bet you can't.

The '90s were the prime time of nipple piercings, belly button piercings, and all sorts of weird places to poke a needle through. They were smart then though, we all gotta live with our tattoos now.

If you were a grunge/metal/hardcore kid who listened to Marilyn Manson or Gwar, then you probably had a lunchbox that functioned as a backpack (in the most ironic cartoon version available).

Back in the day, New Balances came in just one colorway: boring. And you know what? We loved it. The running joke was that computer programmers loved the brand because of its drab colors. Yeah, well now Steve Jobs is planking on billions and you saved your money from working at the Apple store to buy a pair of the J. Crew x NB 1400 collabos.

If you owned an argyle sweater vest, it was from Phat Farm. The brand's dark denim was on point too, with the logo on the back pockets. Stunting!

Benetton's '90s boom came from their awesome rugbys and controversial ad campaigns featuring AIDS patients, bloody newborn babies, and other grotesque imagery to prove that in the end, people of all races are equal.

Before Wayfarers made their comeback, it was all about Oakley Straight Jackets and similar frog-eyed shades. Seriously, you were NOT cool if you didn't own a pair of these.

Ill-fitting vertical block stripe shirts were prevalent in the '90s. Made by everyone from Tommy Hilfiger, Eddie Bauer, Polo, and the like, we'd be remiss if we didn't say they were at least kind of awesome. We'd rock them if they were tailored to today's standards.

When these hit the scene on the feet of athletes like Dominique Wilkins and Michael Chang, we lost our shit. The Pump was absolutely mesmerizing and we had fresh memories of self-lacing shoes in our heads. We felt like the future of footwear was happening right before our eyes and it was awesome!

A staple on boy band necks come wintertime, these came in two varieties: extra-thick for the sensitive guy, and close-cut, dark, and ribbed (for whose pleasure exactly?) on would-be badasses.

You always knew a Guess jean by looking at a chicks ass and recognizing the upside-down triangle on her cheeks. The denim overalls were the best, too.

Cuba Gooding Jr. as Tre Styles in Boyz N The Hood always wore the flyest shit, including hella rayon shirts. Made us wish we worked in the mall so we could get that sweet ass discount.

Carl Jones and T.J. Walker initially wanted to create "clothing without prejudice" to boost social awareness when the duo spawned Cross Colours in the early '90s. At a time when teenage runaways, AIDS, and racial discrimination was clearly evident, the South Central based brand become the beacon of aspiration. Arsenio Hall, Kriss Kross and even the characters on A Different World rocked and supported the brand to "educate and elevate."

First of all, the ladies loved this crap. Second, it was pretty pricey for something you got at a mall kiosk. Which meant if you had one, the girls were definitely feelin' the swag.

The abbreviation for "For Us, By Us," which was supposed to be a conscious movement to support black businesses, was actually worn more by white kids than their black target audience. FUBU still pops off in Asia, believe it or not.

If you shopped at Burlington Coat Factory 15 years ago, then you know exactly what's up.

Better known as Scooby-Doos because of how people would lace 'em loose and floppy like Scooby's ears, wearing the brightest color was a way to get the ladies to stare.

Two words: Grant Hill!

Mossimo was really tight in the '90s and competed with brands like Stussy and others in the urban/active apparel industry. These days, it's known for being one of the brands at Target. Interpret that as you wish.

You had to let these hoes know what time it was. "Call me, 143 637." Texting these days is way too effortless. Kids can't even spell in numbers anymore.

Popular in the late '80s thanks to Jam Master Jay and LL Cool J, it came back in the '90s thanks to Damon Dash, Ghostface Killah, and Rakim. Guess we somehow realized Gilligan had swag all along.

The baggier, the better. C'mon—you had to have been awesome to walk in these.

What better way to rep your crew and piss your mom off than to destroy the backpack she just spent $40 on? Awesome.

One of the funniest things that came from Levi's in the '90s was this Spike Lee commercial featuring much-maligned comic artist, Rob Liefeld.

Rider Strong, Joseph Gordon-Levitt, and Jonathan Taylor Thomas made millions of Asian-American kids look awesome and we thank them for it.

The brainchild of executive producer Oli "Power" Grant, Wu Wear was just a way for the fast-rising group to diversify their bonds. The array of leather jackets, cargo shorts, hoodies, footwear and T-shirts were memorable for the way they all tried to incorporate the iconic "W" symbol.

Shoes with lights in the heel. Awesome for stunting around with your friends in middle school; horrible when trying to run from the cops at night.

This trend kept companies like Dep and L.A. Looks afloat for years.

There was nothing fresher than a new pair of 6-inch wheats, and you were really a pro if you cleaned them with your pencil eraser.

Karl Kani is best known for its ad that featured Nas, (the one which Jay-Z mentioned in "Takeover"), and being the king of '90s fashion in New York.

No Fear was most regularly worn by kids incapable of performing any high-adrenaline stunts. However, the associated cool of extreme skier Glen Plake turned the balls-to-the-wall statement into a school hall staple.

Everyone from Kid from Kid 'n Play, Bo Jackson, and even the X-Men's Colossus rocked this hairstyle back in the day.

If you were from New York, you couldn't wait to save your money and hit Delancey street for an Avi, and you were a boss if you copped the indian head joint.

Your style icon is Brian Austin Green from the O.G. 90210. While he was busy making out with Tori Spelling, Luke Perry was banging Jennie Garth's character. As soon as he lost the lone earring, the style gods awarded him with Megan Fox. True story.

The air-cushioned boots come in all types of colors, and even though Doc Martens are still a trend now, they were huuuuge in the '90s. Street kids in the UK made it one with punk and mod culture, which then made the boots establish themselves into grunge and every other "indie" trend imaginable.

Yo, what up, Sidney Deane? Sick Colnago bike cap with the flipped up brim. You still see this style rocked by maniac fixie bike messenger types, but back in '92, Mr. Snipes had this look on lock.

Nautica was killing it in the '90s with its jackets, shirts, and shorts. The bright colors and the preppy sailboat aesthetic was embraced by urban culture and put the brand in the same lane as Polo and Tommy Hilfiger.

Checkboard Umbro shorts ruled the early part of the decade. Short shorts, yes, but ownership was required for all. Boxers peeking out, sadly, all too regular.

When rappers start endorsing designers in their songs, it's only a matter of time until the fans start picking up the brand. Not only peppering brands like Versace and Moschino in his lyrics, the late Notorious B.I.G. shouts out Aussie brand, Coogi in "One More Chance" back in the summer of '95. The brand known for its vibrant knits should have definitely cut Biggie a hefty check.

B-boys, athletes, grandpas, and British rockstars. All cool. All track jacketed up. Especially in Adidas' three stripes.

Heroin chic was not just a look, but a lifestyle, and CK1's unisex fragrance made you think you too belonged in the androgynous Calvin Klein ad campaigns.

Layaway was tight because it was the only way you could afford to buy that Super Nintendo from Roses on whatever cash you were picking up from your Taco Bell graveyard shifts. It was delayed gratification at its finest, and a sorely missed institution in the day of credit card debt and PayPal.

The Gap had the best pocket tees, anoraks, chinos—you name it—in every color you could want. The Gap made basics cool. If you wore head-to-toe Gap, you were set.

Thanks to Wu associations, Clark's Wallabees enjoyed renewed popularity during the 1990s. The crepe soled shoes were equally cool in urban and prep circles (—the hallmark of a really good '90s trend is crossover). Some folks dyed them. Others beat them to the ground. Ghostface was the undisputed champion.

Tommy Hilfiger was everything. Girls wanted to look like Aaliyah, and guys wanted to be like Grand Puba. Or Puff Daddy.

All we're saying is, if you had an EastPak, that was like going to school with your Power Rangers knock-off toys. Nice Super Human Samurai Syber-Squad figure! Not. JanSport was the real deal, Holyfield.

Who needs a belt when you got a hoodie knotted around your CK jeans and Veruca Salt T-shirt?

Cargo Pants were like SUVs for your legs. It's no wonder why both things experienced such a boom in the '90s.

Slapping yourself on the wrist was never more fun. Plus, these bracelets came in all the craziest '90s prints.

Ralph never fell off, but the '90s were the heyday of the Polo Bear and the Polo Sport brand. Don't act like you don't remember that blue-bottled cologne. The American Flag icon almost became as prevalent as the Pony, and this era of Polo went on to inspire brands like Acapulco Gold.

Flannel may have made a comeback thanks to the whole Americana thing, but in the '90s, flannel shirts were never buttoned unless you were the Bounty mascot.

We remember when we first saw Chuck D from Public Enemy rocking his cap this way, but Will Smith in the height of the '90s is who made us want to rock our caps backwards. Plus, it looks cool as shit.

Starters let you rep your team while stunting in the brightest and shiniest colors at the same time. But fuck around and you had it snatched right off your back.

Michael Jordan won SIX championships in the '90s. That fact alone made us believe that wearing Jordans gave us magic powers. (Also, they still do.) Each pair of Js released during this era was a banger. Every pop culture icon in the '90s rocked a pair. Undeniably the greatest trend of the '90s.