So yes, you can wear a short skirt, but balance it with a draped blouse, boyfriend blazer or an oversize sweater like the one Rice is wearing below. Photo by Emma McAlary 5. If you do a bright red lip, only put a little bit of mascara and eyeliner on your eyes. The essentials for a casual and sexy outfit: You want to, er, walk a fine line between comfortable and slightly sexy. Step away from the crop top, honey.