1. SXSW, 2014

Kanye in a kilt. Yes, a kilt.

2. New York, November 2013

Kim & Kanye both rocked ripped denim for a night out in the city.

3. Yeezus Tour, 2013

What’s that mask, Margiela?

4. New York, 2013

He invented the leather jogging pants, Hedi Slimane.

5. Paris Fashion Week, 2014

His mink may not be dragging on the floor, but we’re sure PETA still doesn’t approve.

6. Paris Fashion Week, 2012

All black errrthang.

7. Paris Fashion Week, 2012

Kim is the yin to his well-dressed yang.

8. BET Awards, 2012

Kanye keeps up with Kim in another matching ensemble.

9. Coachella, 2011

That one time he wore a women’s shirt by Celine and looked fabulous doing so.

10. Paris Fashion Week, 2011

The front row fixture is always a stylish standout.

11. New York Fashion Week, 2011

Lots of layers as he keeps things lowkey in a pair of Air Jordan Infrared 6s.

12. MTV VMAs, 2010

Raise your hand if you, too, have a thing for very deep v-necks.

13. MTV VMAs, 2009

That one time he accessorized with a bottle of Henny. And by accessorized, we mean drank before interrupting Taylor Swift on stage.

14. Grammy Awards, 2009

Shimmer, Kanye, shimmer!

15. Flaunt Magazine Anniversary Party, 2008

Everything about this look was, well, everything. The oversized bow tie, the Louis Vuitton shawl. All of it.

16. American Music Awards, 2008

Remember Pastelle? It was Kanye’s clothing line that never was.

17. NYFW, 2008

He may not have graduated from college, but he gets an A+ for this scholarly look.

18. Essence Music Festival, 2008

Adding another meaning to the phrase “backpack rapper.”

19. Grammy Awards, 2008

Swagger so bright it glows in the dark. Literally.

20. GQ Magazine Anniversary, 2007

Now THIS is a guy who looks like he should be on the front cover of a magazine.

21. Hot 97 Summer Jam, 2007

There are NOT the Red Octobers.

22. Mission: Impossible premiere, 2006

The Louis Vuitton Don himself

23. Brit Awards, 2006

Kim’s ass wasn’t the only one he wanted to dip in gold before, apparently.

24. Grammy After Party, 2006

Wait? What exactly did he tell us? We were too distracted by his loud lavender suit.

25. Grammy Awards, 2006

Anyone else in the mood for a little taco meat?

26. Billboard Music Awards, 2005

A casual Kanye in a cardigan and crisp khakis.

27. MTV VMAs, 2005

He was on his suit, no tie, ish.

28. Grammy Awards, 2005

Got a fresh cut, straight out the salon, b*tch!

29. Pre-Grammy brunch, 2005

The 70s called….And Kanye didn’t answer.

30. BET Awards pressroom, 2004

No, that award was not for being the best dressed on the red carpet.

31. MTV Europe Music Awards, 2004

BYE (Before Yeezus Era), he was still a god–a god of argyle and other pastel-colored preppy pieces.

32. American Music Awards, 2004

And here he is, dripping swagu.

33. BET Awards, 2004

Not one, but TWO Jesus pieces. Or better yet, Yeezus pieces.

34. MTV TRL, 2004

He was basically a proprietor of Polo.

35. Lifebeat Hearts and Voices Benefit, 2004

Ugly Christmas sweaters should really only be worn at ugly Christmas sweater parties.

36. Pre-Grammy brunch, 2003

Ralph Lauren was borin’ before he wore him.

You May Also Like