Why a Saucy Pencil Skirt Is This Fall’s Staple

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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.

Photographed by Arthur Elgort, Vogue, August 1995

The Row Anaste collarless leather jacket, $2,790, matchesfashion.com; The Row Rabina stretch-jersey midi skirt, $350, net-a-porter.com; Louis Vuitton vintage heart and flower hair band, $350, farfetch.com; Gucci Ophidia bowling bag, $2,200, ssense.com; By Far Kim black silk shoes, $426, byfarshoes.com

Photo: (from left to right) Courtesy of matchesfashion.com; Courtesy of net-a-porter.com; Courtesy of farfetch.com; Courtesy of ssense.com; Courtesy of byfarshoes.com
Photographed by Arthur Elgort, Vogue, February 1997

The Range backless ribbed cotton-jersey tank, $100, net-a-porter.com; Versace Collection classic fitted pencil skirt, $208, farfetch.com; Clare V. Le Box bag, $325, clarev.com; Donald Pliner Sana nubuck sandals, $295, donaldpliner.com

Photo: (from left to right) Courtesy of net-a-porter.com; Courtesy of farfetch.com; Courtesy of clarev.com; Courtesy of donaldpliner.com
Photographed by Arthur Elgort, Vogue, February 1997

Aritzia Wilfred Free Elsie sweater, $98, aritzia.com; Roberto Collina, $197, farfetch.com; Staud Shirley PVC and leather tote bag, $210, mytheresa.com; Stella McCartney faux leather mules, $565, net-a-porter.com; Alexander Wang gold and silver watch band bracelet, $395, ssense.com

Photo: Courtesy of aritzia.com; Courtesy of farfetch.com; Courtesy of mytheresa.com; Courtesy of net-a-porter.com; Courtesy of ssense.com
Photographed by Steven Meisel, Vogue, March 1998

Khaite Lydia sweater, $537, farfetch.com; Prada striped rib-knit midi skirt, $780, farfetch.com; Ximena Kavalekas Violy python tote, $1,740, net-a-porter.com; Sam Edelman Hazel pointed-toe pumps, $120, farfetch.com

Photo: (from left to right) Courtesy of farfetch.com; Courtesy of farfetch.com; Courtesy of net-a-porter.com; Courtesy of farfetch.com
Photographed by Arthur Elgort, Vogue, August 1995

Thom Browne coat, $2,900, farfetch.com; Rochas checked pencil skirt, $660, farfetch.com; Chanel vintage CC logo hair clip, $1,273, farfetch.com; Mark Cross Rear Window overnight mini glossed-leather tote, $3,795, net-a-porter.com; The Row Bourgeoise leather slingbacks, $850, mytheresa.com

Photo: (from left to right) Courtesy of farfetch.com; Courtesy of farfetch.com; Courtesy of farfetch.com; Courtesy of net-a-porter.com; Courtesy of mytheresa.com
Photographed by Arthur Elgort, Vogue, February 1997

Theory Wendel stretch-jersey turtleneck top, $130, net-a-porter.com; Roberto Collina fitted pencil skirt, $197, farfetch.com; Louis Vuitton mini Pochette, $310, us.louisvuitton.com; Agmes mini Laila hoops, $295, theline.com; Tamara Mellon Liaison 55 suede shoes, $450, orchardmile.com

Photo: (from left to right) Courtesy of net-a-porter.com; Courtesy of farfetch.com; Courtesy of us.louisvuitton.com; Courtesy of theline.com; Courtesy of orchardmile.com
Photographed by Steven Klein, Vogue, March 2001

Joseph fitted blazer, $181, farfetch.com; Alexander McQueen high-waisted crepe pencil skirt, $595, matchesfashion.com; Mari Giudicelli Jeanne sandals, $144, shopbop.com; Kate Spade Watson Lane bag, $230, katespade.com

Photo: (from left to right) Courtesy of farfetch.com; Courtesy of matchesfashion.com; Courtesy of shopbop.com; Courtesy of katespade.com

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