This last year I switched from boxers to boxer briefs. MUCH more comfortable. I'm really skinny and my hips are much wider than my waist, so the elastic in boxers actually cause them to go up pretty quickly and giving me last wedgies all day. I can't believe I put up with that for about 10 years...
At school, I wear jeans, band T-shirt and sweatshirt or a button up shirt.
At work in the office, I wear khakis with a polo or button up shirt but when I visit plants, I wear jeans.