Would you be more interested in a woman who dressed in stylish, youthful clothes, or one who wore full-length dresses and old-lady blouses buttoned up to her neck? Which one do you think would be more fun to hang out with? Beyond that, would you want to hang out with that dude who insists on wearing a tie and carrying a briefcase to class? Think of your target audience, then go for the look most likely to attract it. Good advice. I think part of being a gentleman is making others feel comfortable. Wearing a pinstripe suit to college class every day isn't going to do that. Having said that, I see no reason why you couldn't step it up a notch and wear some nicer duds. Quality, polished shoes, clean, fitted clothing in general and maybe even an occasional sportcoat over some decent jeans.