Check out this dude, Hakanphotography. Probably my biggest inspiration for fashion, even though he only photographs women. Haha. Had a scuffle with my girl over a pair of jeans, and made me think of him.
P.S. He also has lots of nude work, so if you're not in to that... check it out anyway.
...and Wooster men don't dress like this because...? If you're a collegiate, then I say be as pretentious as you want. If it's a comfort issue... then suck that shit up. There are plenty of clothes out there that are both comfortable and stylish. High effort equals fashion.