"Until you're fat" is the right answer at any age. Denim does not flatter the large of ass. Being over 50, I consider it best to stay far away from any crazy pocket stuff (True Religion), and don't go with too low a rise. I hate pre-distressed so that's not even a question. When combined with a pure white dress shirt, jeans look classic at any age. With a rock band tee, or any printed tee for that matter, it looks like I'm trying to be a kid. Also no Chucks IMHO.
9/18/06 at 1:30am