How to Style a Pencil Skirt the Modern Way
The fashion world's love for nostalgia is clearly showing with the comeback of early 2000s styles, and one piece that's making a big return is the pencil skirt. But what is a pencil skirt? This classic figure-hugging workwear staple first became popular during the women's liberation movement in the '50s and '60s. Now, it's being reimagined in various skirt shapes on the runways, styled in fresh ways that make it feel exciting all over again. Whether in shiny sequins or rich colors, or as a part of a wool two-piece set—we witness how this office essential engulfs the fashion world.
If you're looking for ideas on how to style one yourself, check out the best pencil skirt outfits for women below that blend street style with the hottest trends and confident chic.
Maxi with a Sleeveless Top
Autumn can sneak up on us pretty quickly, and it's not unusual to have some strange weather days, jumping from scorching sun to heavy rain. That's why we love this outfit idea. A maxi pencil skirt paired with a sleeveless top gives you tons of layering options. Wear it as it is, or throw on a jumper or trench coat if it gets chilly. Modify this ensemble with accessories to create pencil skirt outfits for a party or a special event.
The classy pairing—the Pencil maxi skirt with the Sleeveless knit top from House of Dagmar—is a solid base you can dress up for work, casual meet-ups, or when the winter cold hits—with the right outerwear, of course!
Wrap skirt with a Shirt
When you picture pencil skirts, most likely you think of stiff button-downs, but it's time to switch that up. Go for loose, flowy shirts that exude a chill vibe. Breezy long sleeves add movement and keep things looking fresh with your more structured look. As for the skirt, choose something eye-catching—a wrap, an asymmetric design, or a piece with a slit to enhance the laid-back silhouette of the ensemble.
A shirt or a blouse and a pencil skirt is a must-have combo to have in your arsenal. For this look, we suggest the Fluid stripe shirt from House of Dagmar teamed with the Flannel wrap skirt from Erika Cavallini.
Knit skirt with a Matching jumper
The cozy season is officially here, and this outfit is a perfect pick for fall/winter dressing. A matching set with a comfy jumper and a pencil skirt will keep you warm and give you a fashion-forward look. If you are bummed about saying goodbye to your summer co-ords, meet an awesome alternative. Classy and elegant pencil skirt outfits are now as easy as pie.
It doesn't have to be a real two-piece set; you can match items in the same tone regardless of the brand and even material. Here, we paired the Relaxed-fit roundneck pullover from FTC Cashmere with the Ribbed-knit pencil skirt from Erika Cavallini. Crafted in a similar hue, this duo brings the texture to the central point.
All-Black
This outfit is perfect for a night out, whether you're heading to dinner or hanging with friends. The pencil leather skirt hugs your curves, while the stylish details from the top and accessories keep things classy with a bit of an edge. Choose slim-fit black tops to wear with a pencil skirt for the most flattering look.
The Button-detail leather skirt from House of Dagmar is our focal point. Enhance its bold look with the V-neck ribbed top from Erika Cavallini, featuring a deep V-neck and cut-out details on the shoulders. Play around with minimalist accessories and finish the look with a pair of kitten heels so as not to overwhelm the entire ensemble.
Suede Skirt with a Coat
Suede skirts have seen a resurgence in the last couple of years, and they're here to stay, evolving into various styles. We love these textured pieces a lot. The knee-length suede pencil skirt is a classic, but you can modernize it with the help of a short trench coat, matching tights, and a statement belt.
Styling a pencil skirt was never so easy. Pair the Suede midi skirt with the Short trench coat from Tiger of Sweden, throw a long-sleeved tee underneath, and complete the combo with ankle boots—you are ready for your weekday routine and weekend adventures.
Athletic Denim Skirt
If you have a jersey shirt, a sweatshirt, or a hoodie in your wardrobe, pair it with a denim pencil skirt next. This is the perfect formula for casual pencil skirt outfits that feel more elevated than jeans. If you're looking to add a twist to a traditional denim skirt, the asymmetric design or lace inserts can give your classy staple a fashion-forward boost.
The Denim asymmetric skirt from Beige Brown is an ideal piece for this pairing. Combine it with the Short-sleeve cashmere hoodie from FTC Cashmere, add a pair of low-top sneaks, finish with a spacious tote. You've got yourself a relaxed attire, where the pencil skirt shines in an unconventional way.
Maxi with a Denim Jacket
Maxi high-waist pencil skirts are the sleekest options we have in the range of pencil cuts, and normally we tend to style them elegantly or at least smart. Yet, modern fashion allows us to pair not only contrasting colors and textures but also contrasting styles. What if you pair a sleek black maxi with a casual from-top-to-bottom denim jacket? Here comes urban street style.
Let's team the black Maxi skirt from Beige Brown with the Oversized vintage denim jacket from Agolde and a basic white tee underneath. Don't underestimate the power of contrasts.
Denim skirt with a Polo and Sneakers
Go all in on the sporty aesthetic with a long-sleeved polo shirt and comfy sneakers. Use the pencil skirt as a base piece to ground your look, incorporating different colors and textures. It'll serve as the neutral you need to play around with your shoes and top.
Our foundation here is the Reworked maxi skirt from Citizens of Humanity. Let's pair it with the Longsleeve polo shirt from Beige Brown to follow the sporty style with a preppy touch. Sneakers might not be the most common shoes to wear with a pencil skirt, but hey, when they suit the look—go for it. The Curly-effect wool sneakers from Voile Blanche definitely suit this outfit.
Cargo skirt with a Vest
Pencil skirts usually lean dressy, whether you think about them in the context of office wear or dinner dates. However, we find them incredibly cool when they're styled in a more casual manner. On mild autumn or winter days that call for laid-back attire, pair yours with a windbreaker, a raincoat, or a puffer vest and a cool handbag.
We'll use the modern take on the classy pencil style—the Cargo-pocket midi skirt from Erika Cavallini. Mix it with the Long sleeved t-shirt from Lisa Yang and the Puffer vest from Moose Knuckles, and we bet you've never thought that a pencil skirt can be such a versatile essential.
Przeczytaj więcej
Join us as we dive into the denim world, discovering how to style jeans for any occasion and curate the best jeans outfits for men that will turn heads wherever you go.
Explore inspirational ideas for monochrome outfits in various shades to kickstart your single-color outfit game.