The Best-Dressed Men In Hip-Hop


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It seems strange now that hip-hop was once fashion’s rejected child, obsessed with brands but largely locked out of the party. Now, rappers front campaigns for the world’s biggest fashion houses, snap up most of the front row spots and take home all the gongs on award show red carpets, even if they’re still not being recognised enough on-stage.

Without rap’s rise there would be no high-end streetwear, no mixing of skate brands and couture. There wouldn’t be a black designer at the helm of Louis Vuitton. And fashion would be a worse place for it, these best-dressed lists still populated by actors in suits in varying shades of grey and navy. Instead, thanks to hip-hop fashion, menswear is everything, colour and pattern, silks and chiffon, a riot of fun and individuality. And these are the men driving the change, who’ve shown that, with a give-no-fucks approach to getting dressed, the rules of what goes with what don’t have to mean anything.

Kanye West

We almost disqualified Kanye this year for some seriously off-base accessories choices. But when he wasn’t wearing that hat, he showcased a style that’s shifted gears from look-at-me to quietly confident. We’ll wait until his id catches up. In the meantime, he remains a breaker of brands and an instigator of trends – he led the charge on neon and we’re waiting to see how many copy his NYFW tuxedo and sandals look – although this year he also showcased a dadsier side to his wardrobe, albeit still distinguished by things like Gosha x Carhartt work jackets and one-of-one sneakers. Fingers crossed he loses the MAGA collab for 2019.

Kanye West Kanye West

Travis Scott

This was the year that Travis Scott transitioned from a man with a good wardrobe into a full-blown fashion killer. Perhaps it’s the confidence that comes with becoming a father, or notching your second number one album, but in 2018 his everything-at-once approach transformed into an inch-perfect mixing of high and low fashion, of on-point collaborations, of murdered-out Alexander Wang military-wear at the Met Gala. A year ago, his psychedelic vibe would have put him near the bottom of the list for a Saint Laurent campaign. This year, who else would they choose?

Travis Scott Travis Scott


Pharrell’s made himself a fixture on this list by dint of an unswerving dedication to the extraordinary. In what was, by his standards, a quiet year, he still managed to rock full-look Chanel to the Met Gala, a short-suit tuxedo at the City of Hope Gala, and make sports sunglasses a thing. You can see that genre-bending approach to fashion in every other rapper who blends streetwear with couture, but even in his fifth decade, Pharrell still leaves most of them for dead.

Pharrell Pharrell

Kid Cudi

There he was, in a hoodie and ankle-length trench, at Virgil Abloh’s beyond-hyped Louis Vuitton debut. It was an unexpected appearance from a rapper whose style tends to fly below the radar, both on and off the mic. But then, when you’re collabing with Kanye, you should expect on your wardrobe to up its game too, and this year the Kids See Ghosts star swapped his leather jackets and band tees for suits both track- and tailored, and even a dip into scumbro territory with a pair of tye-dye shorts on SNL. Sure, not everything landed. But this felt like the year Cudi embraced a style all of his own.

Kid Cudi Kid Cudi

A$AP Rocky

It was yet another year of fire fits for Rocky, heavy on Calvin Klein 205W39NYC (fitting, for the world’s biggest Raf Simons fan) but also head-to-toe Dior Homme, for pal Kim Jones’ debut, and Louis Vuitton, where he sat front row for Virgil Abloh. So far, so standard. But 2018 was the also the year we saw a stripped-back Rocky, where all-black tailoring and layering won out over colour. It smacked of a man who, finally, feels truly comfortable in his own wardrobe.

ASAP Rocky ASAP Rocky


The 33-year-old Atlanta rapper describes his style as, “Everything”. Which translates as the uncanny ability to be wearing a Palm Angels tracksuit one minute, a Dior Homme suit the next, and make the transition seem like the most natural thing in the world. The sense one gets from seeing him either on stage or red carpets is of a man who loves clothes, whose always loved clothes, for the sense of power and identity they grant when they’re worn just right. And trust, Future always wears everything just right.

Future Future

The Weeknd

On paper, Abel Tesfaye’s approach to style is simple – stick to staples from the world’s best brands and don’t deviate from black unless you have to. But hey, it works. He branched out a little further this year – just check the fluffy HAL 9000 jacket, from Undercover’s autumn collection, which he rocked at the Victoria’s Secret Fashion Show. But in the main, we got the black jeans, the black denim jackets, the black bombers, that worked for him last year and will look just as good in 2019. Well, if it ain’t broke.

The Weeknd The Weeknd


At the 2017 Brits, Stormzy turned up in a fitted-to-death Burberry suit. Cue the pandering applause from those men’s mags that are always astonished when a rapper wears tailoring that fits well. This year, he rolled up in a metallic silver Richard James number, finished with boxfresh Adidas runners. It marked the transition from the Stormzy who always kills his look onstage to the Stormzy who can demolish a red carpet too. Which is handy, considering how many of them he’s on these days.

Stormzy Stormzy

Wiz Khalifa

Wiz Khalifa is cool. The kind of cool that transcends clothes, that seems to seep out of the man inside them and imbue everything he touches with a kind of ineffable awesomeness. He seems to always be on the verge of floating away, which is perhaps why his shirts never seem to stay on his body for very long. What clothes he does wear tend towards the airy, as diaphanous as his own spirit (and the fug of weed smoke through which he travels). It’s impossible to say why he looks good, just that he does, in a way no one else can seem to emulate. Which is pretty much the definition of cool, in our book.

Wiz Khalifa Wiz Khalifa

Lil Pump

Being an 18-year-old multimillionaire, Lil Pump tends to dress like an 18-year-old millionaire. But the ‘Gucci Gang’ rapper won’t die wondering. There’s the hair. The neon. The endless clashing of patterns and colours. He’s a particular fan of an eye-popping knit, be it emblazoned with a Gucci tiger or all-over camo. And while it might not be to everyone’s taste, it’s at least evidence that when you commit to something wholesale, a look that seems to make no earthly sense can actually come together. Although, like we said, it does help if you’re an 18-year-old multimillionaire.

Lil Pump Lil Pump


Drake is basically a 1980s football fan. He loves Stone Island, bleached jeans, bomber jackets and, we assume, showing Millwall fans who’s the real hard nut. It’s a look that shows the value of simplicity and the importance of fit, although for Drake, that means an oversized knit here, a skinny biker jacket there. His wardrobe is also testament to how quality can be the difference between an outfit you’d wear on the sofa, and one that works at the Grammys.

Drake Drake

Kendrick Lamar

Ever since he foreswore “designer shit” for “White tees and Nike Cortez” on his ‘Control’ verse, K-Dot’s style has tended towards the unshowy; some black jeans here, a varsity jacket there, the kind of kit you’d expect to find in the wardrobe of a guardian of true rap. But he’s always had a swaggy side, too – a few years back you’d find Public School shirts and Hood By Air pants in his rotation – and this year he’s let it shine, rocking Craig Green on-stage at the Grammys, then head-to-toe Versace to collect his Best International Male award at the Brits. He still nails the tees-and-jeans look, mind. But now it seems the World’s Greatest MC™ is gunning for the fashion crown, too.

Kendrick Lamar Kendrick Lamar

Lil Yachty

Most well-dressed rappers have a stylist to thank. But Lil Yachty just loves clothes, to an almost unhealthy degree. In August, he let Complex into his closet for a peak at his $100k sneaker collection, which featured pretty much all the Off-White x Nike Ten, Kanye’s unfindable collab with Louis Vuitton, and the Eminem Air Jordan 4s (current resale price: £20k). The same month, he teamed up with resale site Grailed to get rid of some rare Supreme, as well a chunk of Raf, Margiela and Undercover heaters. It was a collection predictably big on colour and pattern, just like the man himself.

Lil Yachty Lil Yachty

Young Thug

It takes some going to out-shine Kanye, but Young Thug’s acid-green leather trench and snakeskin pants combo at the Versace AW19 show did just that. Literally. But then, Thugger has never met a pattern he didn’t like, a shade of neon he couldn’t make work. It’s a lot, but when it’s all mashed together with this much swagger, it seems made for this anything-goes menswear moment. That said, we can understand why the man’s always in sunglasses. He must need something to take the glare off.

Young Thug Young Thug

Jay Z

We’re not quite sure how it happened, but somehow Jay Z – he of sick bars and whack threads – quietly became one of the best-dressed guys in the game by embracing, of all things, the suit. Now, Jay’s always worn tailoring well, but mostly in that nice-and-precise red carpet way. For 2018, however, he’s pairing Calvin Klein 250W39NYC tailoring with graphic tees and chains, and white DBs with mesh vests, all of which makes for the kind of quietly confident style that befits a rap game colossus. It also means he never clashes with his silk-and-sequined wife on the other side of the stage. Although we’re sure that’s coincidence.

Jay Z Jay Z


If you’ve been tempted by a tactical vest, checked trousers or pair of circular sunglasses this year, you’ve got Skepta to thank. Always adept at navigating the liminal spaces between sportswear and luxury fashion, in 2018 he leaned in hard to high-end, appearing on every front row that mattered. He’s also proved a master of gear shifts; in February alone, he wore a velvet frock coat and a tie-dye Burberry puffer jacket, and made both look completely natural.

Skepta Skepta

Tyler, the Creator

There aren’t many rappers who can make bucket hats and pastel cardigans work, but somehow, Tyler, the Creator has turned Florida retiree into a legit look. It helps that, with his tye-dye shirts, BMXs and leopard-print hair, he always seems like he’s bunking off school to go and build a treehouse in the woods. And it’s that naive, embrace-the-difference vibe that makes his wardrobe so strong, a collection of unexpected notes that looks like no one else in hip hop.

Tyler the Creator Tyler the Creator

Chance The Rapper

Whether he’s sitting front row at Ralph Lauren’s 50th anniversary show, or courtside watching the Chicago Bulls, Chance the Rapper will be wearing his ‘3’ baseball cap. The number supposedly stands for his third mixtape, since Coloring Book was too long to fit on, or perhaps the Holy Trinity, a nod to his faith. Whatever the reason, it’s proof that a signature accessory can make even a run-of-the-mill look – from a sweatshirt and jeans to a black suit – feel distinctive if you pair it with the one piece you wear to death.

Chance The Rapper Chance The Rapper


Versace Versace Versace Versace. You can’t accuse Migos of not practicing what they preach. This year, though, the Atlantan trap trio’s branched out into Prada banana bombers, Alyx’s war-ready tactical bags and, when the occasion demands, Dolce & Gabbana tuxes. Basically, whether it’s streetwear or high-end, if it’s luxe and swagged-out, odds are it’s hanging in the closet of either Offset, Quavo or Takeoff.


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