Not an American, so I can't really tell you what's appropriate (in my opinion) for dressing a certain way.
Look dude, just dress the way you fucking want, but like I said here there's a point where it becomes sort of roleplaying, but most people usually dress the way they feel like they identify with the best.
Maybe I'm just assuming too much but I get the feeling that a lot of people on Veeky Forums are trying way too hard to find a "look", just buy clothes that you like and make the outfits come together, it's not that hard.
One thing you should take into account though is that different colours look good on different people, generally speaking stronger colours/contrasts work better on darker skin. There's a picture for that floating around somewhere online.
Personally, I dress very conventionally most of the time, a bit like OP's pic but with more layers and perhaps a bit more of an upper class-ish style. I do however wear experimental and trendy stuff as well, but it just doesn't work out wearing trendy and flashy stuff every single day.
A side note, but important to take into account, as cheesy as it may sound, is that fashion is an extension of yourself and serves to identify which social group you belong to. I usually quickly think about what I'll do during a day prior to picking my outfit, just like you dress up for a job interview you should dress the way you want people to perceive you. Clothes are one of the fastest way to identify and stereotype a person based simply on the way they dress. Keep that in mind.
That's also why I dislike stuff like terrorwave because people are essentially roleplaying, but sure, if you want to be perceived at best as a hooligan and as worst as a nazi or something go ahead.
Anyways, to answer your question in simple terms, just remember skin tone is important when buying clothes and that you have an advantage in a sense that you can buy clothes that people with paler skin can't pull off.