11 of 25
Man on the Moon II, Kid Cudi: No one has ever looked so dapper while sad.
12 of 25
Thriller, Michael Jackson: That is the face of a man who knows he is creating a monumental fashion moment by wearing a black zip-up asymmetrical shirt under a white suit, and not even forgetting to tuck in a snazzy pocket triangle.
13 of 25
Page One, Joe Henderson: How Joseph Gordon Levitt wishes he were dressed all the time.
14 of 25
Help!, The Beatles: Because proper outerwear is always stylish. There's nothing fashionable about shivering or getting soaked for lack of jacket.
15 of 25
Acid Rap, Chance the Rapper: 2013 was a big year for trends we thought would never come back into style: Birkenstocks, jumpsuits, and tie dye. Chance paved the way with his trippy debut cover.
16 of 25
Horses, Patti Smith: This cover doubles as a visual aid on how to nail both androgyny and messy beach waves.
17 of 25
Wolf, Tyler the Creator: Tyler gets points for getting two outfits on one cover, and for transforming a buttoned-up cat shirt into cool streetwear.
18 of 25
Overgrown. James Blake: How Men Should Dress in Cold Weather 101.
19 of 25
Gulag Orkestar, Beirut: The cover photo was torn out of a book found in Leipzig, but could have been torn out of an Anthropologie catalog.
20 of 25
Electric Lady, Janelle Monae: A testament to the pixie cut, mod style, and a great red manicure.