Regarding your statement that "dress pants are more comfortable." I don't think that necessarily has to be the case. For example, I have some RRL straight leg jeans which have a nice slim line but a longer rise; I don't find them uncomfortable in the least. And even dark denim can take a pretty good beating, and so they are "more comfortable" than dress pants in the sense that you'll never have to worry about whether someone is spilling some beer on you, etc. Here's a pic of what I'm talking about, by the way: http://www.ew.com/ew/gallery/0,,2036...769074,00.html It seems to me that this would walk a happy medium between what you are wearing right now and what a well dressed, stylish college student might wear. I was just looking at that picture. I'll also look into those jeans.