The fashion crowd’s enduring penchant for nostalgia finds its apotheosis in the revival of early aughts essentials; in the last few seasons, that affinity has surpassed tailored blazers and pinstripe vests to bring us back to the figure-hugging pencil skirt.

A workwear staple that gained popularity during women’s liberation of dress in ’50s and ’60s, the pencil skirt—both knee-length and midi—was featured heavily on the fall/winter 2025 runways, styled in novel ways that made the old and familiar feel new again. Dries Van Noten cast it in shimmering sequins; Saint Laurent sent down a parade of richly-toned options, and Gucci gave a modern take on the wool two-piece set. For inspiration on how to wear it yourself, you’ll find nine ideas below that nod to both Fashion Month street style and the season’s top trends.

Vogue’s Coveted Pencil Skirt Edit:

The Fall Floral With a V-Neck Cardigan

For an effortless day-to-night night, temper Erdem’s mix-and-match florals with Almina Concept’s blush pink V-neck cardigan, then elevate with elegant extras like Neous’s sheer lace sling-backs and Completedworks’s drop agate and pearl earrings.

The High-Gloss Midi With Argyle Sweater

Heritage codes read decidedly modern when you pair &Daughter’s argyle sweater—a pattern you’ll see everywhere this season—with J.Crew’s patent leather ruffle-trim skirt. Ground the look with studded Prada Mary Janes and top off with a Gucci Jackie 1961 bag.

The Animal Print With Pop of Red

The season’s newest skirts come in a variety of colors and patterns, like this one from Dries Van Noten. Show off your layering chops by styling a cashmere button-down shirt with a black—then adding an energizing burst of red.

The Tuxedo Skirt With an Oversized Button-Down

Take styling notes from Carven’s pre-fall collection by pairing this ever so classic skirt with an oversized button-down. Grey socks and burgundy slides make the look overall feel less formal.

The Butter Yellow and Neutral Pairings

Kallmeyer’s satin pencil skirt, in a minimalist-friendly pale yellow, is easily one of those forever pieces. Pair back it to a cropped knit cardigan (as the brand styled it, too) and neutral extras.

The Luxe Leather With Everyday Basics

For a skirt silhouette that is both season-less and totally on-trend, the answer is Khaite’s Loxley— here in leather, but a core piece you can find in satin and suede as well. Contrast the piece’s warm chocolate brown tone with texture and soft color in the form of a blush pink poplin shirt and a cozy cream knit knotted around the waist or loosely draped over your shoulders.

The Minimalist Choice With a Scarf Cape

Keep your look streamlined with a simple turtleneck or classic tee, topped by Cos’s soft wool cape. Create shape at the waist with Déhanche’s belt, then complete with Khaite’s knee-high boot for a practical meets polished finish.

A Party-Ready Option With a Baby Blue Poplin Shirt

Sequins were everywhere this season. No longer reserved for the evening (or the holidays, for that matter), Roksanda’s midi feels daytime-appropriate when paired with a blue poplin shirt and patent leather kitten heels. An endless celebration tour awaits.

The Effortless Essential With a Trending Funnel-Neck Shirt

Simple is often best—and it doesn’t get better than this Prada pencil skirt. Eschew the formulaic (crewneck, pointy pump) for a more directional styling approach: a leather funnel-neck shirt and a pair of metallic sandals give it cool modernity.