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The 10 Most Fashionable Men Of 2009

Submitted by on December 20, 2009 – 1:45 pm19 Comments
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What we have based this list on are men who can effortlessly go from fresh street wear to dapper formal wear.

It includes rappers, an athlete, and a couple of R&B crooners. We also took into consideration those who take risks once in a while – so necessary when it comes to fashion!

Some of these guys may have been looked over in the style department, but we watched them this year…and they were looking good.

We ranked from last to first place. Let us know if you agree:

10. Ludacris

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Although Ludacris hasn’t quite established a “signature” look like some of our other fashionable men have, we had to give him credit for how far his style has come since he first broke out on the scene.

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Luda back in the day

His look is smarter on both the red carpet as well as the streets. He went from a wild afro to a clean shaven head, tailored suits, and grown up street style. We’ve seen him rock flannel shirts, Air Force Ones, brands like Crooks & Castles, Lacoste, as well as Armani suits.


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9. Jay-Z

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Although he may have been considered as a style icon to many previous to 2009, Jay-Z really stepped up his game this year.

While he didn’t sell out that classic hip hop style, he did indeed clean it up. Jay mixed in distinguished pieces like knit cardigans, classy leather jackets, thick framed eye wear, clean high top sneakers from Lanvin to Supra, and raw denim – neither excessively baggy nor skinny. Timbs may have made a big comeback this year, but it doesn’t look like Jay ever took his off!

Another characteristic of Jay’s style? All black everything. The hip hop mogul favors this shade more than any other, from his jackets to sweaters, kicks, and of course the shades that seem to accompany him everywhere.

On top of the brands mentioned, we’ve seen him rock his very own urban success – Rocawear – as well as PRPS and Play Cloths.

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When it comes to red carpet style, Jay-Z has been looking immaculate and sophisticated in well-made suits, and shoes to match.

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8. Trey Songz

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Yet another celebrity who may have been overlooked in the style department, Trey Songz has upped his appeal by ditching his cornrows and adopting clean, fitted apparel.  

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As you can see in the image above, he is just as hot in formal wear as he is in urban gear. We’ve seen him rock the likes of Gucci, Radii footwear, Money Clothing, and most recently one of the hottest new watch brands, Flud.

When we’ve seen him out and about, its in mostly knit sweaters, tees and button down shirts – hence, the reason we picked him for our gift guide to classic button down shirts:

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7. Justin Timberlake

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Justin Timberlake is the epitome of menswear. He’s best known for rocking fitted suits, vests, skinny ties, and of course a crisp pair of sneakers to match. His own clothing line, William Rast, is a hit, and he is not afraid to rep it.

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Like the line, Justin is preppy with an urban edge.

Other brands he’s known to support are J.Lindeberg, Alternative Apparel and Polo.

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6. Diddy

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Diddy helped shaped urban fashion, we can’t deny that. From his Sean John brand to his seemingly never-ending variations to the classic tux, his look usually screams luxury.

Most often seen in suits, he is known for adding some bling to them – incorporating shiny, textured fabrics, two tone colors and more.  His casual looks are pretty simple – you may catch him in a Rocksmith tee, leather jacket, denim, and Nike sneakers, etc.  We saw him bust out a velour tracksuit last year – a bold move considering the trend has been quiet for some time now.

Most recently, he collaborated with the streetwear brand, Supreme, for a photo shoot and interview. Many criticized the move on both Supreme’s and Diddy’s end, accusing Supreme of “selling out” and Diddy for just trying to stay relevant by connecting with the ever-growing skate/streetwear market.

Perhaps it is Diddy just staying on top of his game?

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5. T.I.

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T.I.

Even though he’s been locked up for a good chunk of ’09, T.I. still deserves some shine for being stylistically on point.

His signature tilted beanie, his street swag, and the way he cleans up in a suit got him on this list. His clothing line AKOO, which he is known to proudly rock himself, is a polished urban line with smart cardigans, crew neck sweatshirts, rugbys and more.

Other brands he’s been spotted in include Carrera, CAVI, and his all time favorite – Polo.

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4. Chris Brown

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Chris Brown in YRB

Chris Brown has undoubtedly had a dismal year, but we’re here shed some light on at least one area he has grown in – his fashion style.

He is clearly a huge fan of skate inspired clothing, rocking brands like The Hundreds and Supra, as well as high end designer labels like Helmut Lang and Gucci.

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Michael Jackson being one of his idols is evident in red carpet and on-stage outfit choices Chris has made. He has confidently worn the marching band jacket, a “Thriller” inspired red patent leather jacket and many more looks adopted from the King of Pop’s wardrobe.

Some may argue that Chris’ style has been slightly clown-ish, but he is a young lad experimenting with fashion and at least taking risks. His style has definitely become more subdued since he first launched his music career.

Where he scored some major points was ironically his court appearance outfits. The gray check suit seen below was fresh:

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3. Pharrell

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Pharrell‘s unique style translates from his music to his fashion sense.

He has two hit clothing brands under his belt: Billionaire Boys Club and Ice Cream. The lines are playful streetwear creations that reflect one aspect of Pharrell’s style. Then there are his more posh looks, as we can see by his ad for Louis Vuitton.

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He pushes the envelope with pieces like his Hermes handbag (or “murse”), the brown boots pictured above, and his studded Christian Louboutin sneakers.

2. David Beckham

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Soccer star David Beckham can go from refined to urban and remain extremely fashionable throughout the process.

He rocks a sexy rugged look in the streets with baggy distressed PRPS jeans, Kanye West x Louis Vuitton sneakers, Abercrombie & Fitch plaid shirts etc.

When it comes to red carpet looks, he pulls off slim fitted suits in a confident and masculine way. His style can best be described as part hip hop, preppy and mod menswear.

We’re sure his fashionista wife, Victoria Beckham, plays at least a small part in David always looking right!


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1. Kanye West

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And the most fashionable man of 2009 is Kanye West – hands down.

This man is a leader, a true trend setter when it comes to style. As much hate as he receives for his “metrosexual” swag, Kanye knows exactly what he is doing. He adapts flamboyant runway styles into dope urban looks that quickly trickle into the streets and into the wardrobes of fashionable men and women.

Who knows what is going on with his much anticipated Pastelle line, but Kanye has launched one of the flyest sneakers of 2009 – the Air Yeezy – along with his hit designer collaboration sneaker with Louis Vuitton.

He was one of the first to don the biggest trends of 2009, like double denim, work boots, denim shirts, shorter shorts, and much much more. Perhaps his hottest accessory is his vixen girlfriend, Amber Rose. The two make a fashion power couple who are hard to keep your eyes off.

Some of the brands we’ve seen this fashion icon rock in ’09 are Martin Margiela, Yves St. Laurent, G-Shock, and SUPER.

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Some tough choices had to be made, but there you have it…

Now we’re sure there are those who agree and those with opposing opinions.

Please share your thoughts here, and expect to see a list of the most fashionable women of 2009 very soon!

Main Image: Esquire

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