This is why I cannot abide Uggs, mukluks, or the more extreme variants of the pineapplehead look.
To me, the most classic footwear possible are 14-eyelet Doc Martens, or the classic Chuck Taylor All-Stars. Some baggy BDU pants will always be more stylish and comfortable to me than any designer label crap (note; I'm so hopelessly out of fashion, I can't even figure out what men's pants are fashionable so I can make fun of them.) I don't believe in spending over $30 on a shirt, no matter who designed it, or what it's made of. (Unless it's a Ben Sherman. After all, Meat Beat Manifesto said "that's a a nice shirt".)
This will probably never change. I will always be a somewhat unkempt white guy in an industrial t-shirt, although girls tell me I clean up nice. I guess I'm the rivethead equivalent of this guy, stuck inside the glory years of his youth.