1. Kanye West
Be Bold. Here's a man who's never met a color he couldn't call his own…Kermit green, Sunkist tangerine, Bubblicious pink. Did he stutter? Nope. If you can wear them with the same confidence, we salute you. Just let one color do the talking and keep the fixins simple. Resist the urge to Twitpic the results.
2. Andre 3000
Accessorize. All right, so Andre typifies the Don't-Try-This-At-Home style icon. But there is one sure-fire thing you can steal from his dandydom: No matter how much wattage the dude has packed in his get-up, he always manages to anchor things with a signature accessory, like suspenders or a straw hat. Just check out any look from his Benjamin Bixby line.
3. Drake
Choose A Go-To. Toronto's finest and 2010 GQ Man of the Year Drake has been nothing if not sweater-obsessed. The Commes des Garçon addict has been seen time and again rocking Rei Kawakubo's cardigans. Take notes on his above-the-waist game. But if you see him in camo cargos, take caution.
4. Lil Wayne
Go Retro. If you rap about venereal diseases and lollipops, then you're permitted to dress like this, too—face tattoos, lip rings, and all. Where Weezy has secretly won is in quietly co-opting '90s punk chic—his obsession with skinny jeans, Vans, and fedoras has been surprisingly influential.
5. will.i.am
Temper The Weirdness. Here's a lesson in what not to do: over-complicate things. Will looks his best when he dials back the jumbled accessorizing. The more Max Headroom the hair, the more head-spinning the results.
6. Pharrell Williams
Stay Ahead. The O.G. of hip-hop hipsters, Pharrell knows how to hit a trend early and quit it before it's going stale. For instance, while everyone else was rocking New Era fitted caps, he was pulling on fur trappers. Even in the desert. If you want to know what's about to be cool, just check out whatever the BAPE allegiant and Billionaire Boys Club designer is wearing right now
7. T.I.
Elegance Over Arrogance. T.I. knows how to max-out the restorative powers of a cardigan and pair of chunky frames. He's been to jail, but looks like a nobleman whenever he throws them on. His other reputation cleanser? High-end Euro threads from Prada, Gucci, and YSL.
8. Kid Cudi
Don't Fear The Basics. Kid Cudi's got a rep for canoodling with indie kids, both musically and stylistically, but he tempers their influence. He's all about the basics. If he's wearing a leather jacket, it's sharp and trim. Skinny jeans? Yeah, yeah, but not the sausage-cased sort. Sunglasses? And Jordans. Always Jordans.
9. Jay-Z
Age Gracefully. Skinny jeans aren't for everyone though. Especially Hova. (His "knots don't fit," remember?) Instead of chasing trends, his game is all about well-played classics: cashmere cardigans, logo-free tees, and slim (but not too slim) denim. When you're a rolling with B, it's no use fighting for the front seat anyway.
10. Common
Own It. Plain and simple, Common's one good-looking bald man. He keeps his dome clean-shaven, and balances out what's missing on top with a well-mowed beard and a chic black turtleneck.
11. Diddy
Self-Promote. Nearly all of Diddy's outfits echo his oft-quoted line from Get Him to the Greek: "I'm mind-fucking you right now." He achieves this effect with luxy get-ups from Sean John. His own. Damn. Line. Mind-fucking doesn't come cheap.
12. Cam'Ron
Remember The Past. You know that whole "Real Men Wear Pink" wave that crashed awhile back? Killa Cam is the guy that convinced rappers it was OK to ride. Time has not been kind to his trendsetting.
13. Beastie Boys
Evolve Or Die. The white boy innovators have had a fluid style over the years, from grungy defenders of your right to party to bohemian, Tibet-saving intellectuals, to their current all-grown incarnation. Today you're more likely to see them suited and booted than smashing Bud cans together. It's called growth.
14. Lil B
Make It Fit. This Bay Area web sensation is constantly pushing the boundaries of exposure and form in his music. Same goes for his necklines. Be very afraid when the Based God tells you where to shop for tiny T-shirts.
Be Bold. Here's a man who's never met a color he couldn't call his own…Kermit green, Sunkist tangerine, Bubblicious pink. Did he stutter? Nope. If you can wear them with the same confidence, we salute you. Just let one color do the talking and keep the fixins simple. Resist the urge to Twitpic the results.
2. Andre 3000
Accessorize. All right, so Andre typifies the Don't-Try-This-At-Home style icon. But there is one sure-fire thing you can steal from his dandydom: No matter how much wattage the dude has packed in his get-up, he always manages to anchor things with a signature accessory, like suspenders or a straw hat. Just check out any look from his Benjamin Bixby line.
Choose A Go-To. Toronto's finest and 2010 GQ Man of the Year Drake has been nothing if not sweater-obsessed. The Commes des Garçon addict has been seen time and again rocking Rei Kawakubo's cardigans. Take notes on his above-the-waist game. But if you see him in camo cargos, take caution.
4. Lil Wayne
Go Retro. If you rap about venereal diseases and lollipops, then you're permitted to dress like this, too—face tattoos, lip rings, and all. Where Weezy has secretly won is in quietly co-opting '90s punk chic—his obsession with skinny jeans, Vans, and fedoras has been surprisingly influential.
5. will.i.am
Temper The Weirdness. Here's a lesson in what not to do: over-complicate things. Will looks his best when he dials back the jumbled accessorizing. The more Max Headroom the hair, the more head-spinning the results.
6. Pharrell Williams
Stay Ahead. The O.G. of hip-hop hipsters, Pharrell knows how to hit a trend early and quit it before it's going stale. For instance, while everyone else was rocking New Era fitted caps, he was pulling on fur trappers. Even in the desert. If you want to know what's about to be cool, just check out whatever the BAPE allegiant and Billionaire Boys Club designer is wearing right now
7. T.I.
Elegance Over Arrogance. T.I. knows how to max-out the restorative powers of a cardigan and pair of chunky frames. He's been to jail, but looks like a nobleman whenever he throws them on. His other reputation cleanser? High-end Euro threads from Prada, Gucci, and YSL.
8. Kid Cudi
Don't Fear The Basics. Kid Cudi's got a rep for canoodling with indie kids, both musically and stylistically, but he tempers their influence. He's all about the basics. If he's wearing a leather jacket, it's sharp and trim. Skinny jeans? Yeah, yeah, but not the sausage-cased sort. Sunglasses? And Jordans. Always Jordans.
9. Jay-Z
Age Gracefully. Skinny jeans aren't for everyone though. Especially Hova. (His "knots don't fit," remember?) Instead of chasing trends, his game is all about well-played classics: cashmere cardigans, logo-free tees, and slim (but not too slim) denim. When you're a rolling with B, it's no use fighting for the front seat anyway.
10. Common
Own It. Plain and simple, Common's one good-looking bald man. He keeps his dome clean-shaven, and balances out what's missing on top with a well-mowed beard and a chic black turtleneck.
11. Diddy
Self-Promote. Nearly all of Diddy's outfits echo his oft-quoted line from Get Him to the Greek: "I'm mind-fucking you right now." He achieves this effect with luxy get-ups from Sean John. His own. Damn. Line. Mind-fucking doesn't come cheap.
12. Cam'Ron
Remember The Past. You know that whole "Real Men Wear Pink" wave that crashed awhile back? Killa Cam is the guy that convinced rappers it was OK to ride. Time has not been kind to his trendsetting.
13. Beastie Boys
Evolve Or Die. The white boy innovators have had a fluid style over the years, from grungy defenders of your right to party to bohemian, Tibet-saving intellectuals, to their current all-grown incarnation. Today you're more likely to see them suited and booted than smashing Bud cans together. It's called growth.
14. Lil B
Make It Fit. This Bay Area web sensation is constantly pushing the boundaries of exposure and form in his music. Same goes for his necklines. Be very afraid when the Based God tells you where to shop for tiny T-shirts.
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