Best Bet: Rogan Geo Skirt

Like the little black dress, a go-to black skirt is a fall wardrobe staple. Rogan accents this tailored wool skirt with soft lambskin leather inserts and welt pockets. It sits slightly higher on the hips, creating a slimming silhouette, and the leather side panels accentuate the waist. As a more understated alternative to full-on leather, Rogan's black-on-black detailing still feels luxe.

Geo Skirt, $135 (originally $295) at Rogan or online.