Khakis P2: ...In fact, there’s nothing that will make you look short & squat like a pair of baggy, pleated khakis. Also, the biggest mistake guys make is dressing khakis up–big fashion foul! Khakis are casual, and never forget it. If you choose to wear them at all, stick with shoes you’d wear with jeans. Because that’s what they are. A jean alternative; nothing more, nothing less.