I'm not good at this style thing (fashion is for girls, style is for guys), so I'll occasionally throw up something for everyone to judge harshly so I can learn more.
I'm very much a tshirt and jeans kinda person, but I'm also somewhat more 'chunky' than I probably should be to make jeans & tshirts panties-removingly sexy, so I'm attempting to resolve that and actually think about what I wear.
I can promise that the thinking won't always work - if at all.
I had to go to a large work function, so I decided I wanted a jacket, but didn't want a button up short because they make me look old. That also ruled out a tie.
Bright tshirts would look tacky, so I decided to find something in muted, darker colours. You can't really see it, but that t-shirt has a Neon Genesis Evangelion print thing on it. It's black print on a purply-grey, so it suited.
Also got some new jeans which are special because they're the first 38's I've fitted (just) in since just after high school. Amazing. Shoes were just a pair of black leather lace-ups, woo.
It's amazing the extra confidence a pair of tighter-yet-not-so-tight-that-my-keys-draw-blood jeans can give you. Or give me. Either one.
The problem I see with what I wore is that I need to get the jacket tailored. I bought it as part of a suit, back when I was at least 15kg heavier. I've also discovered that everyone should get their suit adjusted as soon as they buy it because off-the-rack almost always never fit correctly, so yeah. Interesting to note.