While I cannot particularly understand nor relate to your choices in attire, I must agree with some of the others that you certainly do seem to be comfortable in your style. I am also fairly new to both this forum and the elements of style in terms of clothing, so my view may reflect some ignorance to that end. I see myself breaking several rules that folks here seem to uphold - for instance, I love square toed shoes, and I do wear a black suit from time to time. I also see others here breaking rules that I'd never consider breaking (such as wearing ties with button-down collar shirts). That said, no matter what the style, the one thing that I do is to try and ensure that all my clothes fit me well -- they may not be perfect, but they certainly fit me fairly well, and I certainly do try my best. You seem to be breaking that fundamental tenet in the most brutal of ways, which to me is rather unfortunate. Now, this does not mean that I do not have a handful few shirts that have slightly longer sleeves, or a sport coat that makes me look like a barrel (a skinny barrel, but a barrel nevertheless). But you seem to be going out of your way to wear ill-fitting clothes, which seems unfortunate. I'd merely say that you could still go with your style (whatever that may entail), but wear clothes that are slightly better fitting. I think you will see a world of difference. My two cents.