Wired 25: Kanye West’s Greatest Fashion Moments [Photos] - Page 5
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Hip-Hop Wired takes a moment to tip its hat to one of the freshest MCs to pick of a microphone, Kanye West. And we aren’t talking about his bars.
Since entering the game, West’s fashion choices have risen the taste levels of fans and rap stars alike just as his music has done to improve the culture. That said, Hip-Hop Wired assembles his top 25 greatest fashion moments as we see it. Hit the jump for more.
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Photo: Steve Searle/ WENN
25. Freshman Adjustment (2005)
The stripped rugby is always a classic.
24. Lo-Down (2004)
Funny thing about Kanye. For him to scream on Sway with that “It ain’t Ralph, though,” mumbo jumbo, you’ll be hard pressed to catch him dressed like this anytime soon.
23. Jig-Spotting (2004)
Ye had his swagger right as he spotted the jig. That’s rare.
22. Clean & Simple (2008)
While West’s present day looks display his ability to layer clothing and experiment with pieces juxtaposing in length and materials, it’s simple outfits like this that are some of our favorites.
21. A Bathing Ape (2006)
As you can see, West was just getting into streetwear.
20. Prep (2004)
Months after Jay Z deaded throwback jerseys, West had young men copping blazers.
19. Otis (2011)
Jay and Kanye coordinated looks for their memorable “Otis” video, but the latter managed to standout by layering his white t-shirt with a button down. And he’s rocking the Air Jordan 6, so there’s that.

Photo: Steve Searle/ WENN
18. Bubble Coat (2008)
Again, this is a clean and simple look on West’s part. Also, you’re still liable to see kids wearing a nearly identical fit.

Photo: WENN
17. New Balance (2009)
Of the sneakers West is known to rock, New Balances are definitely a rarity. Appreciate this moment.

Photo: WENN
15. Mixing Materials (2009)
Take your eyes off of Amber Rose for a second and peep West’s fit.

Photo: WENN
14. Leather Era (2011)
Ye came to the 2011 Victoria’s Secret fashion show and tried to outdo the models. We know he did.
13. The Other Side Of The Game (2012)
The pastel mint colored Acne sweater and Air Yeezy 2 “Platinum” combination is one only a few men can pull off.

Photo: HRC/WENN
12. Hypebeast (2008)
2008 was clearly a good year for West, fashion wise.
11. Stunna Shades (2007)
Like it or not, West had grown a$$ men rocking stunner shades and demin vests. Don’t be mad at us, be mad at yourselves.

Photo: WENN
10. 106 & Park (2012)
Yeezy flipped the Nike Air Yeezy 2s a thousand ways.

Photo: Adriana M. Barraza / WENN
9. The Line That Never Was (2008)
At the time, young Kanye West fans like myself couldn’t wait for his men’s clothing line Pastelle to drop. Too bad that it didn’t, because this jacket is crazy.
6. Dead Serious (2006)
L-R-G’s “Dead Serious” hoodie was among the most coveted pieces of streetwear when it hit retailers. Needless to say that West had something to do with it.
5. Don’t Ask Stupid Questions (2015)
“Do you see this coat?”
4. Runaway (2010)
Yeezy made his grand return to MTV’s VMAs in 2010 following the infamous Taylor Swift controversy. It was clearly important to return in style.
2. Grown-Up (2014)
Looks like this one fully personify Ye’s approach to fashion today. He mixes high-end brands while, but manages to make the look connect with the Hip-Hop crowd.

Photo: WENN
1. Game, Blouses (2011)
Yes, this is a woman’s blouse. And no, this isn’t a troll. Part of the reason this look left folks talking is because it was well put together.
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