This is my first post also. I was actually planning on being a silent user on these forums until I read your post and felt rather compelled to respond.
There's a striking similarity between your first paragraph and my own experiences, although I wouldn't use a word quite as strong as "depression", I've certainly had periods where I've felt a little lost and helpless. I firmly believe my image has played a major role in my unhappiness. Hair loss being the number one factor. It's surprising how easily you can lose confidence.
In all honesty I was never that great with fashion anyway, but things were much easier 10 years ago. Logos were more than enough to kill any creative individualism. I always wanted to dress a certain way but as you said yourself, "feel odd, won't fit in"... I think we'll all fit in just fine when we truly find ourselves.
I'm going for a slight edgy, smart casual look (at least that's how I'd describe it) with bright statement accessories (ties, scarves,lapel pins etc), because I believe that's who I am, and I think I'll be much happier and confident.
Good luck to you sir!!