I like to dress a bit on the preppy side, but I still stay away from skinny jeans because I think they look silly on guys. I like to wear vests/sleeveless sweaters and dress shirts with casual jeans and an expensive pair of sneakers. On occasions where that may not be necessary/appropriate, a simple t-shirt (that fits me), shorts/three-quarter pants and one of my pairs of Havainas will do. There's not much variety in the way I dress beyond that because I don't like to spend a lot of money on clothes.

Except shoes. I spend a lot of money on sneakers.