Actually this is something I'm a little bit concerend of too and of what I didn't thought about before. ^^ I bought a bomber, which doesn't look much oldschool at all I think and isn't black or olive, but some kind of blue and also the material is cotton and I wore it with slim, tapered, dark blue jeans (just some Levi's 511 without any obvious wash) and oxblood colored boots, which in my opinion don't look very similar to Docs and stuff like that. This, and the fact, that I live in Germany and look somewhat stereotypical German, like, tall with light blond hair, made people think I'm a some kind of neo nazi or skinhead, I think. ^^ Though I like the combination I try to avoid it now and wear the jacket with other stuff like light brown backzip suede boots from APC and tapered pants, preferably not in blue or black and stuff. Which is also nice. Maybe I'm just thinking too much of this stuff and I'm just not self-confident enough, don't know.