Yes, you can wear culottes and look cool. When choosing a top, treat them like any old pair of pants. But choosing the right style is key. Culottes can easily be unflattering and make you look shorter or wider (unless you’re one of those tall thin types who look good in anything). The key is to find a pair that hit a few inches above the ankle and that are fitted on the sides, no bunching or pockets, which can add bulk. Size up if you need to. Add length (and polish) with a pump or sandal, or go low-key with a slide, sneaker, or loafer for a more casual look.