Man, you wear shorts and race t-shirts to work for 15 years, and end up missing the whole fashion thing completely.

Bills is starting to look more attractive. I'm still hung up on the way jeans feel through the crotch. Maybe I can try on a really nice pair and see about the fit, but to get the comfort w/out pleats doesn't seem possible to me if I don't buy big and cinch it with a belt.

I'm still not down with $100+ jeans. There's no cost to a given cut. It's just paying for the texture, pocket stitching and maybe fabric/proprietary weaves. Same with khakis.