The 20 Most Stylish Celebrities Every Year for the Last 20 Years

Image via Complex Original

Thanks to his long hair and penchant for torn-up flannels, River Phoenix looked more like the bassist for Soundgarden than an Oscar nominated actor. His legendary performances (both on and off screen) helped to bring the crunchy Northwestern style of the '90s to the masses. Unfortunately Phoenix met his untimely demise in late '93, immortalizing him as the James Dean of the grunge era.

In 1994, Michael Jordan made one of the most inexplicable decisions in sports history; His Airness (temporarily) left the NBA in his prime to flounder in the minors of the MLB. While Jordan's career never panned out on the diamond, this year was a crucial period for MJ's style. His look was far more reserved than his early technicolor track jacket days, and a helluva lot cleaner than his current all oversized everything stage, making '94 a super-stylish year for number 23.

If MJ embodied a more reserved '90s athlete style, it was Deion "Primetime" Sanders who really blew it out of the water. And we aren't just talking about his signature Jheri Curl. As one of the best two-sport athletes in history, Sanders extraordinary stats were only matched by his epic outfits. Draped in gold chains, laced in tracksuits, and dripping in swag, Sanders looked like Rick James and played like a Hall of Famer.

By '96 rap's King of New York had become the King of the World, and along with all of his musical accolades came the most stylish year of young Christopher Wallace's life. Bouncing effortlessly between tropical-toned Coogi sweaters that would make Riff Raff blush, and imposing three button suits to match Biggie's freshly-minted mogul status, at 23-years-old rap's reigning champ ruled the world of men's style.

In 1997 Will Smith rode that Fresh Prince wave right onto the big screen, and the motor-mouthed kid from West Philadelphia became a bona fide superstar with Men in Black. Leaving his neon 5-panels and overalls behind, Smith emerged as a red carpet ready celeb with black suits and white sweaters to match his more mature work. And yes, we are calling Men in Black mature.

Dressed immaculately in either all-black-everything or all-white-everything most of the time, Puff Daddy's wrist was rarely bare. If his diamond pinky ring wasn't enough of a hint, his luxurious style always made it crystal clear that he had far more money than you. And of course, Puff was never without a pair of dark sunglasses to hide his disapproving glares directed at all the peasants surrounding him.

When Brad Pitt finished shooting Fight Club in '99, he clearly kept a bit of that Tyler Durden panache with him. For the remainder of the year, his style was pretty damn far off the rails. From appearing on the cover of Rolling Stone in a dress, to wearing floral shirts on the red carpet, to his insane looks in Fight Club itself, few celebrities exemplified the sheer absurdity of pre-millenium menswear quite like Pitt.

Back when "Young Hov" was actually young, long before Barclays and Beyonce, hell, even before The Blueprint, there was Jay Z in 2000. He was proudly throwing up the Roc and wearing anything with the Roc-A-Fella name on it. Y2K Jay was the king of repping your clique back when repping your clique was the most important thing in the world. Along with his self-promotional tees, Jay always managed to wear a least one piece of crucial early aughts headgear, from beanies, to sweatband, to durags. This style is super dated at this point, but in 2000, Jay Z was bodying all the top trends of the moment.

The New York rock scene had been on life support for well over a decade when The Strokes emerged in 2001 as the city's shaggy-haired savoirs. Dressed in skinny jeans and leather jackets, The Strokes were helmed by their fearless, fresh-faced leader Julian Casablancas. He was the Mick Jagger of the new millenium, revitalizing a lifeless genre and returning the "New York cool guy" to his all-black throne.

The Diplomats represented that last gasp of unabashed bravado in the New York rap scene, and no one personified this relentless attitude more than Cam'ron. In the rap history books 2002 won't merely be remembered as the year that Killa Cam dropped the classic album "Come Home With Me," it'll also be remembered as the year that Cam wore oversized pink bandana coach's jackets, camo boonie hats, and XXXL basketball jerseys. If rap's swagger peaked in '02, at least Cam'ron took it out with a bang. 

In 2003, thanks to the influence (some would say over influence) of his recent films Blow and Pirates of the Caribbean, Johnny Depp decided that his staid Kentucky roots no longer suited him, and it was time he adopted a more bohemian style. The result is Depp's now legendary modern-day-Pirate-meets-delusional-sixties-rocker look, complete with all the excess chains, blousy tunics, and steam-punk suits that match such an intentionally avant-garde style.

It was just a year earlier that Adrien Brody took the stage at the 75th annual Oscars to make out with Halle Berry. Oh yeah, and to accept the award for Best Actor. But it was in '04 that Brody became an award winner of another kind when Esquire named him the "Best Dressed Man in America," and with good reason too. Brody's ability to wear a suit without looking stuffy made him a clear choice at a time when tailoring was becoming personal again.

2005 was the year that Pharrell Williams graduated. Moving on from The Neptunes, Pharrell stepped out on his own to release his first album, and then, in a move that was arguably even more extraordinary, Pharrell jumped from the sidelines of style to the major leagues by teaming up with Nigo to found Billionaire Boys Club. Bridging the gap between rap and streetwear like never before, Pharrell's all-over print outfits became the definitive look of mid-2000's hip hop.

He was one of the forefathers of modern street skating, but it's quite possible Mark Gonzales' greatest contribution to the sport was recognizing that skateboarding is far bigger than a deck and trucks. Gonz threw art, design, and panache into the equation, and made style one of the most important tenets of modern skateboarding. It wasn't just about how you skated anymore, it was about how you looked while skating.

Leaving the world of professional soccer behind, Japanese Midfielder Hidetoshi Nakata emerged in 2007 as one of the world's best-dressed men. Trading in his jerseys for designer threads, Nakata became a fixture of front rows and magazine editorials across the globe thanks to his uncanny ability to pull off stunner shades, sheer designer shirts, and fedoras without looking like a total douchebag.

What do you do after releasing a handful of the greatest rap albums of all time? Well, if you're Andre 3000, you leave the group to go start your own clothing line. In a move that disparaged rap fans across the world (although he did appear on the "Int'l Players Anthem" in 2008) Three Stacks moved on from Outkast in the late 2000s to stake his claim as one of the world's best dressed men and establish Benjamin Bixby. The clothes mirrored Andre's style, meshing neo-prep with classic southern designs, and while Bixby didn't last, the man himself remains one of hip-hop's most renowned dressers.

2009 was the year Kanye got off that backpacks and Bapestas shit, and high-fashion Kanye was born. From interrupting Taylor swift in a leather button-up at the VMAs, to debuting his own footwear line, to wearing moto jackets at the front row of fashion shows, Kanye emerged in '09 as an aficionado of designer threads. It may look a bit silly now, but Kanye was experimenting with menswear and pushing it past the staid grossness of the mid-2000s.

With the release of The Social Network in 2010, it was obvious that Justin Timberlake had long outgrown his boyband days and was now ready to be taken more seriously as an artist. Well, if you could consider someone who starred in "Dick In a Box" to be an artist. But, one thing was clear—Timberlake's style certainly had come of age. Swapping his graphic tees and baggy cargos for sleek black suits and tie bars, JT proved why he's the only member of 'N Sync who transformed beyond the boy band look. Even though the single was a few years away, Timberlake was already king of the suit 'n tie shit.

While menswear fans ogled at Ryan Gosling's scorpion jacket from Drive and his bespoke suits from Crazy Stupid Love, the actor was clearly taking some notes of his own, as he began pushing the boundaries of style off-screen. Gosling began wearing slim suits, vintage pea coats, and even pajamas around town, helping to redefine Hollywood style in the #menswear era. He won 2011 when he showed up at the Cannes Film Festival in a pajama shirt.

Some artists wait decades for their big break. A$AP Rocky is not just some artist. After releasing his first mixtape just a year earlier, A$AP Rocky hit the music world like a leathered-out, tidal wave of waviness in 2012 with a ferocious concoction of crafty lines and unorthodox outfits that re-interpreted looks from the runway without alienating kids in the streets.

Rocky forever changed the style of modern-day hip-hop when he emerged from Harlem with a closet full of Jeremy Scott, Raf Simons, Rick Owens, and countless other labels that had rarely before been associated with rap. Less than a year later, everyone from Kanye to Justin Bieber have taken cues from Rocky, and Cam'ron's pink furs now seem like nothing but a distant memory.

True to fashion for the Korean music scene, G-Dragon's career isn't easily summed up in one word. The 25-year-old is a true "slashy" and could be described using any configuration of rapper/singer/songwriter/dancer/model/fashion icon depending on what day of the week it is. It's that last category, of fashion icon, that made G-Dragon Complex's latest digital cover star. No one quite balances the streetwear meets high fashion meets avant garde approach quite like G-Dragon, and we can assure you, you'll be seeing countless copycats in the year to come.