8 Ways To Style A Classic Pencil Skirt In 2025

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It isn't an exaggeration to say skirts dominated the streets of fashion weeks all over the world for spring/summer 2026 previews. While 2025's outdated skirt trends were completely off the radar, there was an endless variety of fresh shapes as well as familiar ones reimagined in trendy fabrics and textures. From classic A-line skirts to dramatic pleated silhouettes, there was an endless variety of styles. But one truly stood out above the rest: the pencil skirt. 

While this silhouette may have been the standard for a classic office look, it has resurfaced as a must-have piece for 2025. And it's no longer limited to predictable pairings with blazers or rigid button-downs. In all the forms and styles for 2025, the pencil skirt has taken on a much more modern edge. From styling with crop tops to relaxed-fit sweaters, these skirts are proving they can be more than just an item in your office wardrobe.

If you've been looking for ways to try something new or found a bunch of pencil skirts you just don't know what to do with, the latest styling trends are here to show how chic these skirts really are. The street-style reinventions of pencil skirts highlight just how versatile and current this piece has become. After this, you'll definitely want to go through your closet and see which of your pencil skirts can be refreshed, or perhaps even pick up a few during a fall or winter shopping spree.

If you're the kind of individual that loves to go bold or go home when it comes to fashion, a statement pencil skirt will be your perfect canvas. Zebra, floral, checkered, or other eye-catching patterns can instantly add character to a classic silhouette. You'll want to balance out the styling by pairing the skirt with a crisp button-down. For a more polished look, tuck a white button-down in and add a second statement piece in one of the unexpected colors trending in fall 2025. Or opt for a relaxed-fit denim shirt untucked for a modern, street-style appropriate look. 

Real fashionistas know how to make a tone-on-tone look work without feeling flat or predictable. In 2025, try a pencil skirt in the texture of your choice (whether it's leather, knit, or denim) and pair it with a top in the same hue. If you prefer a darker palette, brighten it up with a crisp white tee underneath, or add some serious character to the overall look with a pop-of-color statement piece such as a bag, shoes, or even a pair of socks. The key is mixing textures and adding a bit of contrast to keep the look modern and effortlessly chic. 

As one of the NYFW street style trends anyone can start wearing in fall 2025, argyle sweaters are perfect for pairing with an edgy, textured pencil skirt. Leather, black denim, or suede pencil skirts styled with a preppy argyle knit top strike the perfect balance between classic and modern. While tucking the sweater in gives it a more work-appropriate, polished vibe, you can also leave it untucked and slightly relaxed for a casual day out. Finish the look with statement sneakers, like the Adidas Tokyos, for relaxed street-style appeal. 

Nothing makes a look more casual than a clean white T-shirt, and pencil skirts are no exception. It doesn't matter if it's a patterned number or a solid classic, a basic white tee can soften the formality of a pencil skirt and gives the outfit a modern, approachable feel. For a casual and stylish fall look, try a slightly oversized long-sleeve vintage tee slightly tucked in to the skirt or draping over it. For something seriously bold, a fitted cropped tee adds a contemporary twist. Chic shoes like the Coutgo Mesh Slingback Kitten Heels will create a look that's equally ideal for an evening out or running errands. 

V-neck sweaters work with everything and anything, and pencil skirts are no exception. These classic knits are the perfect way to style pencil skirts in 2025. Whether you like your v-neck knits fitted, loosely draped, or oversized, they add cozy sophistication while keeping your pencil skirt look modern. Fitted v-neck knits should be tucked in, while you'll want to let oversized ones flow over the skirt to create a more laid-back feel. Keep your neck bare and accessorize the look with statement earrings, or layer on a delicate chain or pendant necklace to add a personal touch. 

For that picture-perfect French girl chic, you need to invest in a high-quality tweed jacket. A high-waisted knit or satin pencil skirt creates a elegant silhouette that feels both modern and timeless. Keep it casual by wearing a knit long-sleeve top or a short-sleeve tee underneath. For something more elevated, a lightweight turtleneck or a fitted sleeveless top like the Verdusa Textured Tank Top can add a refined contrast in texture. You'll want to avoid sneakers for a tweed jacket look, as it can as they can be too casual for tweed's refined and polished aesthetic. Instead, opt for ballet flats or mules. 

While there are many jacket styles that are trending in 2025, none feel as current as the barn jacket. And while it may surprise you, this countryside classic has some serious game when it comes to complementing a pencil skirt look. The rugged outdoorsy vibe of the outerwear and the pencil skirt's defined and sleek silhouette strikes the perfect balance between city-meets-country style. The best part? The jacket will easily do most of the work for your outfit, so you can simply throw on any vintage graphic tee or a plain white one and still look put together and on-trend.

What is fall without a good crew neck sweater moment? Everyone has a favorite crew neck or two tucked away in their closet, but it's time to bring them out and give them a stylish update. Pair your best crew neck with a pencil skirt for a balanced blend of comfort and style. Don't go for a fitted version, but instead try a looser, more relaxed fit so that it sits perfectly over the skirt. For added dimension, layer the look with a trench coat or cropped bomber jacket. Top the ensemble off with knee-high boots for a fall-ready outfit.