Your post is somewhat contradictory. You start off by saying that a lot of the fits on SF are "dandyish" and not representative of what you see in real life and then you conclude by saying that you'd like to see people take more risks here. Doesn't make much sense.
not saying dandy is bad, saying that fits here are often great but they tend to conform to a set of rules that do not apply IRL - they are part of a narrow consensus that can afford the occasional challenge - sos gotta buy some groceries ..
I guess I should leave the vest for when I'm dressing up a bit more - with dress shirts and ties.
Also, on the hat, I've grown a big liking for hats, but ever since I've had short hair, I don't think it looks as good. I think my head looks a bit weirdly shaped with it, whereas when I had longer hair, and it would flow from under the hat, it looked better. (Holy shit I need to learn to write shorter sentences, and not just adding commas everywhere :DDD)