How to Style the Classic Pencil Skirt to Look Modern and Cool in Fall 2025
Time to pull your favorite pencil skirt out of the back of your closet. Because even though the piece has always been a wardrobe staple, it’s about to become trendier than ever this fall.
There are some pieces that just seem to be totally immune to fashion cycle. They never leave us, really—they stay muted for a while, only to come back into the zeitgeist so forcefully that, suddenly, they’re everywhere. The pencil skirt is the perfect example. Since the 1950s, the garment has been a quiet, reliable choice for women looking to add an instantly elegant and feminine touch to their outfit. Now, in fall 2025, it’s having a major comeback as a defining piece in several designers’ collections and on celebrities like Daisy Edgar-Jones, Lola Tung, Jenna Ortega, Emma Stone, and Sofia Carson.
These new, more modern pencil skirts don’t stray from their origins. They still feature minimal lines, rigorous and sensual at the same time, that include a high-waist, clean-cut silhouette, and classic fabrics and colors. Now the fresh take on the pencil skirt is all in the styling. Rather than exclusively pairing it with formal looks or office-friendly basics, fashion pros are wearing theirs in more casual, daytime outfits too.
This only proves how timeless pencil skirts can be. Whether you match them with the latest trendy sneakers or a classic kitten heel, they really can suit anyone. This fall our favorite way to style a pencil skirt is to play with its proportions—perhaps juxtaposing the slim skirt with an oversized pullover, a cropped knit top, or a jacket with an exaggerated silhouette.
Edward Berthelot/Getty Images
Raimonda Kulikauskiene/Getty Images
Edward Berthelot/Getty Images
Edward Berthelot/Getty Images
If you’re shopping for a pencil skirt for fall 2025, look for ones that highlight your curves and fall below the knee but above the ankles. The fabric doesn’t matter much: Wool, tweed, leather, faux leather, satin, denim, etc., are all on trend. You can also find pencil skirts with side and front slits that make them more wearable.
Pair the skirt with a blazer for the office, a bomber jacket on the weekends, and a trench coat if you want a more elegant look. A short, cropped sweater will highlight the skirt’s high waist, while an oversized pullover or T-shirt will give the outfit a more laidback air. Pumps and slingbacks are best for the office, but we’re seeing a lot of street style looks incorporate knee-high boots and old-school oxford loafers.
The point is, there’s really not much you can’t style with a pencil skirt. Some things are a classic for a reason.
A version of this article was previously published in Vogue Italy.
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