short dress pants -- the ones short enough to show off your ankle and socks while walking.
manpurse -- not talking about messenger bag or bags with shoulder straps, but bulky "designer" bags looks like you are carrying both you and your girlfriend's grooming kits.
sandals -- I've had my fair share of wearing them (to everywhere) while I was still in school, indeed I didn't care and intented to leave that impression. although I don't do wear them outside my house anymore, but if I see the wearer is likely in college, I'll give him the pass.
square-toe shoes -- already been covered to death.
If I can say something about women's trends, I say snow boots (thought not really sure what they are called)-- as fugly as square-toe shoes for men, especially the ones with furry material on top.