I'm, mostly, a tee shirt and jeans guy. I wear them almost everywhere with my skater shoes. (I don't skate, they are just so freaking comfortable.) There was a death in my family and I had to go out and buy some dress pants and some cheap loafers. I had a black sweaterish shirt I wore. This all got me to thinking that I never dress up at all anymore. I don't really know how anymore. I've been reading a few things on how to dress for overweight males. I could stand to loose 25 pounds. Also I don't have 5000 dollars to start with, but I have a steady income and can get a few things here and there to work my way up. Also I'd rather not start off with a suit, just try to get comfortable in the other clothes first but I'd like a shirt and tie thing heh. Where can I dress up? Church is a given but what about other places where I'd normally do the tee shirt and jeans? Dinner and a movie? So hit me with some quality but inexpensive things. Shoes: Anywhere from 80 to 100 dollars. I'd go 150 if I thought they'd last me for years wearing them a hand full of times a week. Pants: I'm thinking black because it's slimming. Also the guides said no pleats. I honestly don't know what brands are quality. Shirts: Black Charcoal Maroon are the ones that I think would go well with black pants. Am I missing any? Dark colors because they are slimming. I did pick up a black button up shirt with vertical lines. The shirt fits okay but the collar seems to high and makes me feel like I don't have a neck. Is this common? Any help appreciated.