Hah yeah, the old "rap vs. classical" thing. I remember having that opinion when I was 9 years old, then I figured out some things about the world.
I've gotten lots of compliments on one pair of shoes, a pair of black leather Beatle boots. I think it's due to most people's unfamiliarity with the style, combined with how completely rad they looked.
Also, I've had people compliment my Dolce & Gabbana chelsea boots, not for the way the looked, but for the D&G label on the rivet (real cultural cache in a town where the only clothing stores are Urban Outfitters, Macy's, and Hollister).