A wardrobe workhorse, a pencil skirt is something everyone should have hanging in their closet. This no-brainer pick for office-friendly outfits (they work just as well as part of a suit look, or broken up with mix-and-match separates) has a sleek silhouette and is available in fancier fabrics than staid wool suiting—think brocade and even sequins—that translate easily into evening wear. Don’t be intimidated by this skirt’s form-fitting shape, either. Because it sits close to the body and has a long line, this style adds no bulk and actually helps visually elongate legs. Read our expert tips for finding the one that’s just right for you.