Jeans - Carhartt (half the price of levi's, equal quality, easier to take the logo off than Levi's) Do have a pair of black levi's though.
Shirts - American Apparel plain color shirts. Expensive but comfortable and high quality. No logos or brand name in sight.
Outerwear - I have a carhartt jacket that's fleece lined for when it's really cold. Looks almost the same as the day I bought it 4 years ago. Also have a military bomber jacket for every day use. Got the idea from the Gibson novel Pattern Recognition.
Shoes - Either my hiking boots if I'm doing outdoor activity or it's snowing or a pair of black keds. I'm not sold on the keds, they're my first pair. They aren't super comfortable, but they're very comfortable and I get more compliments than with other shoes.

I try to keep it as simple as possible, I like what I wear.