I know what you meant, man. You just gotta have some confidence in what you wear. Swagger if you will. I think everyone is capable of pulling off a pair of stan smith vintages (i prefer the blue tab). Can wear with modern prep type looks, semi-streetwear looks, boring safe looks, or more pretty easy. Leather chucks aren't that much different. I'm just trying to say i have faith in your ability to pull off simple, inoffensive clothes/shoes. If i can get away with wearing what i wore a few days ago in a southern college town, you can wear stan smiths with your raw jeans and black jacket.