Was chatting with a male member here the other day and was astounded about how clueless he is about male fashion; and what constitutes casual vs. dressy for mens shoes and pants. Maybe it's a regional difference, since I am on the east coast and he is on the west. When did khaki pants become dressy? I always thought khakis were casual nice, but not dressy. Therefore a lace up shoe, loafer, boat shoe, or sneaker could be worn with them depending on the occassion. If I saw a man wearing wingtips with khakis I'd think something was wrong with him. To me wingtips are a dress shoe. Are Khaki Pants Dressy? What shoes do you wear with khaki pants, if you ever wear khaki pants? What shoes do you wear with a suit? What shoes would you wear with jeans for a casual date out? Say TGIF's and a movie. Should your shoes match your suit or your socks?