i think everyone should wear what is comfortable to them, and it can be great fun to wear things with references that are relevant to your tastes, and can sometimes make for surprise meetings with people on the street. i’ve had that happen with some of my metal band shirts…it seems to really make their day when they spot me, and that in turn makes my day!
i also wear lots of sci fi and geeky reference shirts, with the same result at times.
having a style is something that is IMO absolutely fine. i know a guy in America who has found real satisfaction in something called Dandyism, which is essentially a resurgence of Victorian men’s fashion. these guys look pretty cool! it’s never something i’d feel comfortable wearing, but they look great in their top hats and often with fantastic moustaches etc 
the only time i personally have a problem with fashion is when it is all-consuming and vapid and changeable as the wind…it is the “all consuming” part i struggle with. i think if fashion is your work or hobby, i can totally understand that…and in itself there’s nothing really “wrong” with it. it’s only a problem if it becomes an idol. and while any of the 499million interests i have almost certainly become idols to me at some point or another, it seems scary to me that many live as if this is ALL that matters.
the knock-on effect of that is the huge amount of pressure put on women (and increasingly on men) to look a certain way: a way that reduces them to their style, or to a collection of body parts, or just throws them away because their beauty is not in keeping with what fashion has dictated is beauty that week. (and we all possess beauty, if we only knew it, just as we are…that beauty can be cultivated if we accept ourselves the way God accepts us, and this largely comes form inside).
actually, that parenthetical point is i think what Jesus might have been hinting at, although actually i think He was perhaps more talking about the basic need to cover with SOMETHING…maybe not fashion.
and then we have naturists, who don’t worry about clothing AT ALL
and actually, i think they have a point…not that i think we should all leap on that particular band wagon…but they actually strip (sorry) away the aspect of nudity that makes it a sexual thing, and just make it normal. it’s a nice idea…and i’m sure it works out well for them that are into it. i believe there are Christians that have this school of thought, but off the top of my head i don’t know any specific groups, and i’d assume they are a vast minority. but talk about the body being worth more than clothes…they really live that 
the main time i personally have issue with clothing is when i am expected to dress a certain way, to look “smart” or “put some effort in”…that really irritates me. there is very little effort in “dressing up” as it’s called, and the idea that it looks “smart” really aggravates me. i am not a different person if you stuff me in a suit. i rebel against this as much as i can whenever i get the chance.