MSD

Depending on my mood and the occasion, the first, third, and fifth categories. I don't go for the hipster look, and I don't wear anything with big obnoxious writing, or anything made by a company known to use severe sweatshop labor, so Gap/Old Navy/Banana Republic and Abercrombie are out on both counts.

I pretty much wear whatever is comfortable, fits the occasion, and suits my mood at the time. My typical outfit, from the bottom up, consists of:
either boots or casual shoes that are good for school, work, and walking,

Khakis, Jeans, or Field Pants (military green, straight pockets, look good with spit-shined boots,) with a braided leather belt,

Either a regular t-shirt or a ribbed t-shirt (not wifebeater, I have a bunch that are really soft and comfortable, look good, and are half rayon/half polyester, so they don't hold odors, sweat evaporates without leaving that nasty smell, so I can wear them multiple times between washings, and anything that touches them can be wiped off with a bit of water.)

These clothes offer me a multitude of options. I can pair khakis with a ribbed shirt, which has the texture of a sweater, and therefore looks nice enough to wear to church, Jeans and a t-shirt for when I don't have to worry about looking nice, and a whole bunch of mix and match options. I usually wear boots, field pants, and a ribbed shirt, which looks good and is comfortable as hell.

In the summer, I wear microfiber skating shorts that come halfway down my shins, and a sleeveless shirt or t-shirt. I can't wear sandals due to flat feet, which really sucks.

In the winter, I go with a regular outfit, and depending on how cold it is, I have a nice Ralph Lauren leather jacket that goes perfectly with anything but formalwear, or an ankle-length trenchcoat that keeps me warm in any temperature avove 0°F (and If I wear all black with it, I look like I escaped from the filming of The Matrix )

For formal occasions, I don't resent having to wear a suit, I actually enjoy it. I have a black suit, nice dress shoes, and a choice of ties. For parties, I tend to dress just like I do daily. For concerts, since most that I go to are some variety of extreme metal, all black usually fits in best, with jeans and an old t-shirt to survive the mosh pit and crowd surfing.