9 Effortlessly Polished Pencil Skirt Outfits to Try This Fall

Photographed by Phil Oh

The Party-Ready Option With an Everyday T-Shirt

J.Crew’s all-over sequined pencil skirt won’t be delegated as an evening exclusive. When paired with Leset’s comfy-casual Margo T-shirt and a pair of strappy Gucci flats (who can resist a sharp toe?), here’s a look that can take you from a celebratory lunch to late-night dancing.

Photo: Courtesy of Getty Images

The Trending Leather With an Oversized Cape

Shopping for a pencil skirt that is both seasonless and totally on-trend for now? The search ends with A.L.C’s Marta skirt. Contrast the rich, moody burgundy with Cos’s soft wool cape, a pair of pierced pumps from Tory Burch, and a woven bucket bag from Bottega Veneta.

Photographed by Phil Oh

The Pop of Color With an Elevated Hoodie

Not long ago, the hoodie was a mere layer to throw on top of your athleisure after an early-morning pilates class en route to a cute café. Allow us to introduce you to a loftier iteration with styling mileage beyond the studio: Aritizia’s zip-up crafted from supple cashmere. Go tonal with accessories and let Tory Burch’s vivid skirt do the talking.

Photo: Courtesy of Getty Images

The Minimalist’s Choice With a Coveted Boot

There’s never a wrong time for an outfit composed of minimalist pieces, especially when one of those pieces is Toteme’s A-line leather pencil skirt. Styling it with a simple crewneck sweater from J.Crew and a thin belt from Déhanche is a no-fuss formula that works for everyday. Khaite’s knee-high Marfa boots are just the cherry on top.

Photographed by Phil Oh

The Textural Touch With a Little Box Bag

Hoping to make a bold declaration this season? Look to Vogue Runway’s Laia Garcia-Furtado who stepped out in emerging brand Lii Studio and its electric teal, fuzzy pencil skirt for that. Accessories, like Aquazzura’s velvet pom-pom slingbacks and Savette’s ladylike top-handle bag, keep the look streamlined but playful.

Photo: Courtesy of Getty Images

The C-Suite Look With Fashion Codes

When in doubt, take a page from Miu Miu’s archives. Below, follow suit by tucking Everlane’s sage green button-up into Cos’s double-faced wool pencil skirt. Complete the look à la British Vogue’s Julia Hobbs with coveted accessories, like Alaia’s Le Teckel bag and Margaux’s patent leather Mary-Janes.

Photo: Courtesy of Getty Images

The Trending Scarf-Sweater With a Runway Favorite

The best of both worlds, the scarf-sweater-hybrid promises all-day comfort and warmth, without the commitment. Versatile and easy, like this one from Rohé, the scarf ties can be wrapped around the neck or left dangling at the nape. Like Vogue’s executive fashion director Lisa Aiken, pair yours with Prada’s peplum pencil skirt, Neous’s wear-anywhere sandals, and Madewell’s affordable bucket bag.

Photographed by Phil Oh

The Metallic Midi With a Classic Blue Button-Down

This season’s newest pencil skirts come in a variety of unexpected fabrics—from suede and leather to crinkle metallics, like this one from Staud. Show off the five-pocket design by tucking in a crisp blue poplin shirt, then add a beaded necklace from Completedworks for a personality wink.

Photographed by Phil Oh

The Effortless Essential With Silky Separates

Sometimes simple is best—and what’s more vital in a wardrobe than a classic black pencil skirt? Offset the ease of this black capsule piece from Max Mara with The Row’s silky embroidered shirt and Rachel Comey’s leather shoulder bag, punctuated by fringe details. Other accessories, like Mansur Gavriel’s Dream ballerina flats, wrap it all up on a tonal note.