A: Shorts at work are a hotly contested topic, and rightly so—I've seen women go very wrong wearing them. Even in jobs with relaxed dress codes, shorts often make you look ready for the beach rather than a meeting. But they can be done right (especially given this season's longer, sleeker styles), if you're careful.
• Try dressy silk crepe or sturdy stretch cotton; avoid flimsy cotton voile and wrinkly linen.
• Shorts should have a plain, full cut—like trousers—and hit just above the knee.
• Think of shorts as you would a skirt. I like them with a pretty blouse, blazer, and bold jewelry.
Add wedges or pumps, or patent leather or metallic flats.
Left: Club Monaco, $130; 212-459-9863. Right: Diane von Furstenberg, $245; 646-486-4800.
More Fashion Advice from Adam Glassman