Image via Complex Original
Yes, you read that right. And no, I'm not being ironic. The '90s weren't just a black hole of JNCOs, Airwalks and Oakleys. There were some game-changing dudes who made the most of plaid shirts and combat boots, neon and stonewash, and of course, East Coast vs. West Coast. From rappers and grunge rockers to TV legends and even a couple of Batmans, we've rounded up the freshest set of celebs that inspired us then and retrospectively entertain us now. (Mortifying teen-magazine poses are just an added bonus.) Enjoy The 50 Most Stylish Celebrities of the '90s.
RELATED: The 90 Greatest '90s Fashion Trends
RELATED: The 90 Best Hip-Hop Fashion Ads of the '90s
RELATED: How '90s Cartoons Influenced Today's Style Trends
RELATED: Green Label - 20 Best Hip-Hop Fashions from the '90s
50. Dr. Dre
Why He Made The Cut: No one's forgotten about Dre's laid-back West Coast steez.
As much as we love "The Chronic," let's face it—Dre is at his best behind the scenes, so it's only right that his personal style be crisp, clean, and just a little under the radar.
49. Liam Gallagher
Why He Made The Cut: Proof that being a dick is fine if you look cool doing it.
When in doubt, err on the side of copying a Beatle. The return of the Lennon frames were alive and well in the '90s. And no one pulled it off better than the "Wonderwall" singer. His unwarranted asshole behavior might have been another story, but at least he looked cool while pissing everyone off.
48. Martin Lawrence
Why He Made The Cut: Martin had us doubled over but no one was laughing at his style.
By nature, stand-up comedians are horrific dressers. But Martin (and a handful of other hilarious dudes later in the list) somehow managed to get it right. Sure, we would have loved if he had a more focused look, but even if a little all over the place, he never disappointed.
47. Spike Lee
Why He Made The Cut: Brooklyn cool before Brooklyn was cool.
When you're known almost more for your eyewear than for your actual work, you're doing something right in the style arena. Spike is the epitome of consistency but also possesses the rare ability to freshen it up subtly. Take notes.
46. Jared Leto
Why He Made The Cut: You may hate him now, but don't deny his status as a '90s trendsetter.
Stay with us. Jared Leto doesn't belong on any list but the worst...usually. But you gotta admit, Jordan Catalano (of "My So-Called Life") was pretty damn influential for '90s slacker style. Plaid shirts, shearling bombers, and choker necklaces could be seen in every high school hallway for the better part of a decade.
45. The Wayans Brothers
Why They Made The Cut: The first family of '90s style.
Due entirely to the cult success of "In Living Color," the '90s were the era of the Wayans (for Damon, Marlon, Shawn and Keenan anyway). Not all their personal getups were as outrageous as the sketch show's signature aesthetic, but between that and a handful of decent flicks (you know you loved "Blankman"), they had the A-List on lockdown...at least until the 17 or so "Scary Movie" installments to follow in the next decade.
44. Pierce Brosnan
Why He Made The Cut: Golden eye for style.
The James Bond of the '90s oozed with British class and style, and as one would expect, cleaned up pretty damn well. Even in his Remington Steele days, Brosnan maintained a rakish appeal, thanks mostly to his hair, which managed to remain suave but just unkempt enough when the action really started going. On the red carpet, he knew how to rock a suit well too. Even if his license to kill isn't real, his license to dress up will never expire.
43. Jamie Foxx
Why He Made The Cut: The early days of this modern-day style icon looked promising.
Also benefitting from some serious "In Living Color" exposure, the stand-up comic and budding R&B crooner used the spotlight to improve his wardrobe game year after year.
42. Matthew Perry
Why He Made The Cut: Could he BE anymore stylish?
Bowling shirts and buttoned sweater vests might not be all that covetable now, but Chandler Bing showed an entire population of dudes with boring office jobs that they too could bag a Monica Geller...or at least fool themselves into thinking so.
41. Eddie Murphy
Why He Made The Cut: Ain't nothing funny about this funnyman's style.
Professionally, the '90s weren't as good to Eddie Murphy as the '80s were (the Klumps, honestly...). But the dude still managed to keep the ban-collar and mock-turtleneck game on lock.
40. Ice Cube
Why He Made The Cut: Not only was today a good day, the entire '90s was a good style decade.
He may have been one of the originators of gangsta rap, but what we loved the most about Ice Cube (that is, before he ever thought daddy movies were a good idea) was that he looked like every other dude from the hood. Jeans, a sweatshirt and a Raiders cap were really all you needed. Then, the lyrics can speak for themselves.
39. Arsenio Hall
Why He Made The Cut: Late-night TV's daily dose of realness.
Arsenio Hall changed the late-night TV landscape with his talk show, but he also knew how to stunt. Take for example, the wild ties he'd pair with simple suits. And when he felt like taking things to the next level, he'd rock multicolored leather jackets and bright-colored blazers. For a guy whose job was to let the guests shine, he certainly knew how to keep the attention on himself too.
38. Nas
Why He Made The Cut: A decade of classic music and classic style.
As Nasir Jones made his ascent as one of rap's greatest talents of all time, he helped bring NYC's outer borough street style into the stoplight. Polo, leathers, puffy jackets, Timbs, and bucket hats all became iconic of the era. Thank the illmatic MC for that.
37. Wesley Snipes
Why He Made The Cut: The freshest dude on the H&R Block.
Between "Jungle Fever," "White Men Can't Jump" and "Blade," Wesley Snipes was at the top of his acting (and styling) game for the entire decade. That is, until his wardrobe went from red-carpet tuxedos to prison jumpsuits some years later. Stupid, taxes.
36. Ethan Hawke
Why He Made The Cut: Star of the slacker generation.
Everyone's favorite Gen X posterboy, Ethan Hawke unknowingly launched an army of thrift-store hoarders rivaled only later to that of...Hipster Millennial thrift-store hoarders.
35. Chris Rock
Why He Made The Cut: Have you seen CB4?
As we've said, comedians are usually complete schlubs. But when your full-time job is to make fun of other people (as Rock so brilliantly does), it's a lot more effective to actually dress better than the butts of your jokes (also as Rock so brilliantly does).
34. Boyz II Men
Why They Made The Cut: Remember when they rocked Jordans to the Grammys?
Okay, we have to admit: Grown-ass men dressed like themed quadruplets is pretty lame in retrospect. But at the time it was fire. From actually making sweater vests look good to their coordinated suit ensembles, their style legacy was established when they all rocked Jordan 11s with tuxedos-people went nuts!
33. Johnny Depp
Why He Made The Cut: Johnny be good.
Before he became a walking display of mewelry and reasons to wash one's hair, Johnny Depp was slaying the style game along with numerous women's hearts. His bad boy/tortured artist image was embodied with plenty of leather, torn-up jeans, and models on his arm. No doubt plenty of dudes copied this steez in the hopes of getting a Kate Moss type wifey.
32. Bill Bellamy
Why He Made The Cut: He taught us how to be a player.
From MTV Jams to an acting career, Bill Bellamy did it all in style. Whether kicking it with Bizzy Bone or balancing an array of lovely ladies in Def Jam's How to Be a Player, there was no doubt he knew what he was doing when it came to getting kitted out.
31. LL Cool J
Why He Made The Cut: From bucket hats to a six-pack, LL stayed fly.
When "Mama Said Knock You Out" dropped in 1990, LL started to carve out his own signature style. Essentially, he kept the bucket hats and chains but went with a lot less sweatshirts and a lot more leather. And it worked.
30. Luke Perry
Why He Made The Cut: He stole our childhood crush's heart, so we stole his style.
A then modern-day (albeit factory-made) James Dean, Luke Perry's loner rebel attitude on "90210" was the teen-hearthrob-magazine thing of legend. A wardrobe rife with Wayfarer shades, ripped jeans and motorcycle boots naturally went hand in hand; although, the whole not-looking-40-while-playing-an-18-year-old thing proved to be a slight side effect.
29. Paulie Shore
Why He Made The Cut: Style isn't that serious, buuuuudddy.
The laid-back SoCal style was perfectly embodied by Paulie Shore. Besides his penchant for wrapping up his curly locks in a headband, almost everything he had was sleeveless. Whether they were vests or cut-off jean jackets, this was a dude who seriously loved to let his arms breathe. Always the stoner buddy in films like Encino Man, his own film career made him a leading man without compromising his eccentric style.
28. Kid 'n Play
Why They Made The Cut: They brought flat-tops to the masses.
Splitting time between hip-hop and comedy is a tricky business. To pull it off both ends of the spectrum, a batshit sense of attention-grabbing style—such as a footlong flat-top and head-to-toe neon—is key.
27. Jason Lee
Why He Made The Cut: The original low-key cool guy.
There was not a nerdy white kid to be found in the mid '90s that did not want to be Jason Lee. He started as a professional skateboarder, appeared in a Sonic Youth video, and starred in multiple Kevin Smith movies. He was sharp, sarcastic and wore a mean corduroy blazer—so, he had all the 90s cool guy essentials down.
26. Hugh Grant
Why He Made The Cut: Sleazy? Sure. Steezy? Definitely.
With a powerhouse combo of the best hair and tie-less suits in the game, Hugh Grant was an unstoppable force. Even his prostitution-sting mug shot was fresh. Wanker.
25. George Clooney
Why He Made The Cut: The classic gentleman playboy.
Thanks to E.R., Clooney got his head in the game. Literally. His Caesar-inspired haircut became the de facto style for dudes much in the same way '90s ladies flocked towards "The Rachel." Besides his influence on '90s grooming, he also knew how to look great in a suit, something he continues to do today.
24. Snoop Dogg
Why He Made The Cut: His clothes were smoking, too.
In the days of East Coast vs. West Coast, it wasn't just who spit what, but also who wore what. And there is no better example of textbook Cali style, than a gangly 6'4" dude in pigtails and a short-sleeve button-up.
23. Woody Harrelson
Why He Made The Cut: White men can't jump, but they can be fresh.
As "Cheers" wound down in the early '90s, the lovable goof came into his own, both on screen and off. And regardless of what he was playing (from a streetball hustler to a psychopathic serial killer), we wanted his clothes. That "Parental Advisory" t-shirt? Game over.
22. Kenan Thompson and Kel Mitchel
Why He Made The Cut: Their style was All That and then some.
Aw, here it goes! Kenan and Kel were two of Nickelodeon's best talents at a time before it was pumping out child stars at Disney-channel levels. Granted, for every Nick Cannon we get an Amanda Bynes, so it went with Kenan and Kel after the '90s. But man, during their heyday, they at least looked fresh. Kel often sported bucket hats and snapbacks, and even rocked gear like Tommy Jeans overalls and chore jackets. Not one to be out done, Kenan often rocked hockey jerseys and patterned short-sleeve button downs. While Kel outdressed him back then, we all know we can find Kenan on Saturday Night Live today-while Kel... well, he was in a KFC commercial once.
21. Mark-Paul Gosselaar
Why He Made The Cut: For better or worse, Zack Morris is the style icon on '90s TV.
No '90s recap--of, well, anything--is complete without an obvious inclusion of Zack Morris. Any suburban white guy from '90 to '93 would've practically parted with a testicle for that blonde coif, closet full of stonewashed jeans and the Kelly-Kapowski-bagging confidence that came with it all.
20. Christian Slater
Why He Made The Cut: Part bad boy, part badass.
Christian Slater is the perfect example of how confidence directly affects your entire appearance. It's not that his v-neck sweaters were any better than anyone else's, it's that he was...Christian Slater...in a v-neck sweater, therefore, inherently badass.
19. Puff Daddy
Why He Made The Cut: Can't stop won't stop stylin' on 'em.
Say what you will about his personal rap cred: Sean "Puffy," "P.Diddy" or "whatever-the-hell-we're-calling-him-now" Combs is first and foremost a businessman. The man signed Biggie for God's sake. (He also produced some of the decade's biggest albums, too.) So it's no surprise he did it all with a calculated sartorial mission--whether it be silk Versace shirts or monochromatic, futuristic track suits--to go along.
18. Stephen Baldwin
Why He Made The Cut: The best-dressed Baldwin—aka "The Blonde One."
Even though Alec made it out of the '90s with a career, Stephen stole much of the spotlight thanks to his golden locks and killer style. Not many men can rock a suede vest or survive as much cocaine as this guy. These days, he might have traded the Booger Sugar for a Bible, but the Sassy magazine archives will live on as a testament to his everlasting awesomeness.
17. Keanu Reeves
Why He Made The Cut: Johnny Utah will always be cool.
One of the most polarizing style stars, Keanu always seems to be the guy people love, hate or love to hate. But whether he shows up on the red carpet in a tux or a beenie, he just never seemed to give a fuck either way. And for that, he's alright in our book.
16. Michael Jackson
Why He Made The Cut: Unique and iconic. MJ ruled in the '90s.
Michael Jackson didn't begin his descent into weirdness 'til the end of the decade, but in the '90s he went from high-water pants and loafers to custom military jackets from Gieves & Hawkes. He also started wearing shades pretty heavily, but his glove remained a style staple.
15. Busta Rhymes
Why He Made The Cut: He put his steez where our eyes can see.
Before Busta Rhymes looked like a jacked-up stegasaurus, he was a skinny kid from Long Island who's flow was as funky as his unique sense of style. When your steez ranges from Chinese emperor to shiny suit man to quintessential early '90s style, and all with crazy dreadlocks, then you're definitely gonna make this list. Busta's eccentric wardrobe was wild as hell, and throughout the decade both his music and style was constantly turnt up to something crazier and even more bonkers.
14. Michael Keaton
Why He Made The Cut: Sharp and funny, one of the decade's greats.
Maybe it's our undying desire to be Batman (or hell, some days, Beetlejuice), but there aren't many people as naturally awesome as Michael Keaton. Put him in a good blazer and forget it. He's cooler than you. Deal with it.
13. Denzel Washington
Why He Made The Cut: He was the man every chick wanted, and every dude wanted to be.
Denzel was not just a man, in the '90s, he was the man. In the same way dudes like Ryan Gosling get fawned over, that was Washington at his prime. Managing to project a nice demeanor while performing in some of the roles that would come to define his career, Washington not only embodied '90s style, he was in a lot of the decade's greatest films.
12. Jerry Seinfeld
Why He Made The Cut: His style was about nothing. Which made it great.
Puffy shirts aside, Jerry had his shit together. Almost in the way his comedy was really just about nothing, his personal style was subtle, genuine and right on point. I mean, what's the deal with double-breasted?
11. Jay-Z
Why He Made The Cut: He went from businessman to a business, man.
He may not have hit the mainstream scene until '97. But right from the start, Hov's style was crisp, modern and well ahead of its ("all black everything") time. Need it bear repeating, he also cofounded one of the most successful urban fashion lines to date--Rocawear in '99. So, trust.
10. Ghostface Killah
Why He Made The Cut: The Wallabee Champ couldn't be stopped, or topped.
Pretty Toney was always one of the most vocal handlers of the Liquid Swordz, but also one of the clique's most stylish. From du-rags under snapbacks to ridiculously awesome gold accessories like the eagle bangle, Ghostface was also known for his rather extensive Clarks Wallabees collection. Even though it was Raekwon who pushed the Polo movement forward, Ghostface rocked the covetable gear too, but flipped it to match his own eclectic style, which is why he edged him out as Wu-Tang's most stylish member.
9. Michael Jordan
Why He Made The Cut: In his heyday, his Airness was fresh as hell.
Today MJ's wardrobe might be something we cringe at, but the greatest of all time had dope clothing back in the day. Whether on or off the court, during the '90s Jordan could seemingly do no wrong. His steez may have fallen off, but the '90s were the glory days of Air Jordan, and we can see why everyone wanted to be like Mike.
8. Beastie Boys
Why They Made The Cut: Progenitors of hip-hop street style.
As the first (and greatest) nerdy Jewish rappers in the game, Michael Diamond, Adam Yauch and Adam Horovitz won us over by never pretending to be anything they weren't, artistically or stylistically. And we still wear those damn Adidas Campus sneakers to this day.
7. Tupac Shakur
Why He Made The Cut: He was a true original who helped define hip-hop style even today.
Front-knot bandanas. Stomach rocker tattoos. Dickies chore jackets. Timberland boots. Tupac embodied the thug life beyond his lyrics, he looked the part too. His lasting impact on hip-hop style can be seen on everyone from 50 Cent to Kanye West. Even when they digitally resurrected him at Coachella, he was rocking a bandanna, baggy jeans, and 6-inch wheat boots. Looks like Thugz Mansion has a minimal wardrobe.
6. Leonardo DiCaprio
Why He Made The Cut: Effortless style in a decade of trying too hard.
If Leo hadn't turned out to be such an unbelievably badass actor, we'd hate his fucking guts. He was wearing unbuttoned silk blouses for like five years straight...and still looking better than the rest of us. Again, it's all in how you pull it off.
5. Andre Agassi
Why He Made The Cut: FEAR THE MULLET.
In the '90s, Andre Agassi dressed like the wild meth-smoking crazy person that he was. Playing a sport with no team uniform meant he could bring his personal steez onto the court. Agassi was so into being the most stylish player on the court that he abstained from playing in Wimbledon because of the traditional all-white dress code. Talk about commitment to the style game.
4. Deion Sanders
Why He Made The Cut: The '90s were Neon Deion's time to shine.
No other athlete of the '90s embodied the decade more than the trash-talking, high-stepping, and flashy-dressed Deion Sanders. Simply known as Prime Time, Sanders dressed the part - dripping in gold and draped in clothing that was as brash and as flamboyant as his charismatic personality.
3. Will Smith
Why He Made The Cut: He was fresh before he was Big Willie.
Being the Fresh Prince alone would've been enough to lock Will Smith in a spot on the list. But more than just an insane collection of Air Jordans early on, Will made the nearly impossible (and seamless) transition into sleek, mature red-carpet styles. Coincidentally, his blockbuster status wasn't far behind.
2. Kurt Cobain
Why He Made The Cut: He didn't invent grunge, but he made it cool.
A trendsetter in more ways than angsty two-chord songs, the Nirvana frontman will always comes top of mind at even the slightest mention of the flannels and ripped jeans the grunge era is known for. That and we're also partial to his carefree approach of incorporating Kool-Aid hair dye and even women's leopard print. Let's all stop taking shit so seriously.
1. Notorious B.I.G.
Why He Made The Cut: His style was the reason he always saw some ladies that could be havin' his baby.
Biggie Smalls is the '90s. For many reasons, but music and larger-than-life personae aside-Coogi sweaters, Kangol hats, gold jewelry, Versace shades, and big man swag that couldn't be matched. He even rocked turtle necks, newsboy caps, and gigantic white suits with admirable aplomb. Plain and simple, he's the king. All hail B.I.G.