Tight to the body, straight across, and above the knee: The pencil skirt has many fans. It’s the corporate signature of executives, the go-to garb of your college religion professor, the Dewey Decimal–loving librarian. But much like the dowdy cardigan gone wild, the tame pencil skirt has a saucy side, too. There are plenty thigh-high slits and hiked-up lengths, as well as embedded thong straps (memorably seen back in Tom Ford’s Gucci Spring 1998 collection).
Though more often than not, coaxing sex appeal from a pencil skirt comes from the wearer’s creative styling liberties. Look to the late ’90s for inspiration, when the piece was often worn with a slinky tank top to offset its modest silhouette. In more recent years, Kim Kardashian West has taken it for a spin, too, wearing her skirt with tube tops. As for around the Vogue office? “Style it with a simple black tank or turtleneck, as well as kitten heels. You can wear it from work to a date,” says Market Editor Anny Choi, who has been wearing the wardrobe staple recently. “My fall closet changed after I scored a vintage Dolce & Gabbana one off The Real Real for $30.”
In other words, don’t skirt the garment. Here, shop the season’s best versions.