Wolf, I got a question for you. I've pretty much had a complete wardrobe redesign since high school. In high school and before, all my clothes looked like crap, as my mom bought them at Walmart, but I'm generally kinda rough on clothes, so they'd be resewn by me (my mom didn't know how to sew really) and then a lot of my other clothes were, say, surplus military clothes, cuz I liked them. I also had a phase where I liked military surplus clothes and plain black tshirts, but people got wrong ideas about me (ie, school shooter type stuff) from wearing that sorta stuff, so I stopped.
Now I'm pretty much at the opposite extreme, I wear "preppy" clothes. You know, Hilfiger, American Eagle, Abercrombie, Polo, all that kinda stuff. I buy it used for quite cheap and good condition at Salvation Army or Goodwill. Honestly, they're quite good clothes. I've noticed the more expensive brand shirts tend to actually fit better than, say, a cheap brand Hanes shirt. Like they make you look less fat kinda fit better.
But, the problem comes. I feel like, people, while just on chance encounters judge me more favorably based upon me wearing "preppy" kinda clothes, and see me more as a "normal person" if that makes sense. So in essence, dressing like that is camouflage. But I feel like the problem is, people make their initial impression of me, but then when they talk with me, I don't like....match, if that makes sense. Like I look pretty "bro" or "preppy" I guess, and then people talk to me, and they're confuzzled because it's not my personality type at all. Have you run into such a problem as this? I don't have any issues with the clothing, and it's genuinely nice clothing and I enjoy wearing it, but like, should I wear "nerdier" clothes so people think I'm a "nerd" or what? Or screw it all, they're just clothes I buy for like a dollar, and they just cover my body. Heh, no idea.
Anyway, if I can add a tip, regarding being confident about your body. I'd say 99% of the time, do NOT wear loose shirts and clothing. This was one of my issues. I'd wear all kinds of loose clothes because I was overweight, but then it just ends up that you look more overweight, as you're trying to cover the fat "lines" with the clothes, but the clothes themselves are loose and add more like, mass to your figure, if that makes sense, and people still see your bodyfat levels in your face anyway. If you do wear looser clothes, I feel the best strategy is have either the top or bottom of you loose or tight, and the other the opposite. IE, looser fitting shirt and then tighter pants, or vice versa. I mean in my case, I can pretty much wear a medium of most brands of shirts, sometimes even a small in some brands, and wearing a large in most any brand looks dumb on me.
EDIT:
Wolf, in regard to proportion, I have a question. I have huge legs and a huge butt, but my upper body is pretty average/small. I'm like a meso-endo somatotype, I guess. Generally I wear 34x30 or 36 jeans, I was in 32s before squatting, I don't believe I'll ever be in 32s again even if I get to a low bodyfat level. And again, usually medium tshirts, sometimes small, almost never large shirts. So should I in your opinion, wear looser jeans or tighter ones? Girls have commented on my huge butt positively, but it's always been something I've felt in the back of my mind like, odd about. And again, loose clothes sometimes make you look fatter, I feel like I fit best in looser 34s and tighter 36s.