Winter fashion doesn’t have to mean bulky layers and shapeless outfits. Pencil skirts are a stylish and versatile piece that can be worn even in the colder months when paired with the right layers and accessories. From cozy sweaters to elegant coats, there are endless ways to style a pencil skirt for winter. Whether you’re heading to work, a casual outing, or a special event, these winter pencil skirt outfit ideas will help you stay warm while looking effortlessly chic.
50+ Winter Pencil Skirt Outfit Ideas:
Classic Turtleneck and Wool Pencil Skirt – Stay warm with a fitted turtleneck tucked into a wool pencil skirt for a polished winter look.
Chunky Knit Sweater and Leather Pencil Skirt – Combine textures by pairing a thick knit sweater with a sleek leather pencil skirt.
Long Coat and Neutral Pencil Skirt – Layer a long wool coat over a neutral-toned pencil skirt for an elegant winter outfit.
Tweed Blazer and Pencil Skirt Set – Opt for a matching tweed blazer and pencil skirt for a timeless winter office look.
Faux Fur Jacket and Midi Pencil Skirt – Add warmth and glamour with a faux fur jacket over a midi-length pencil skirt.
Oversized Sweater and Belted Pencil Skirt – Balance an oversized knit sweater with a belted pencil skirt for a flattering silhouette.
Plaid Pencil Skirt with Knee-High Boots – Style a plaid pencil skirt with knee-high boots for a trendy and cozy winter outfit.
Cashmere Sweater and Velvet Pencil Skirt – Go for a luxe look with a soft cashmere sweater paired with a velvet pencil skirt.
Turtleneck Bodysuit and High-Waisted Pencil Skirt – A sleek bodysuit tucked into a high-waisted pencil skirt keeps you warm and stylish.
Trench Coat and Wool Pencil Skirt – Layer a classic trench coat over a wool pencil skirt for a sophisticated winter look.
Monochrome Outfit with a Pencil Skirt – Wear a matching top and pencil skirt in the same shade for an effortlessly chic winter ensemble.
Pencil Skirt with a Puffer Jacket – Stay warm without sacrificing style by layering a puffer jacket over your pencil skirt outfit.
Cable Knit Sweater and Corduroy Pencil Skirt – Pair a cozy cable knit sweater with a textured corduroy pencil skirt for extra warmth.
Layered Tights Under a Pencil Skirt – Stay warm by wearing fleece-lined tights under your favorite pencil skirt.
Wool Blazer and Midi Pencil Skirt – A wool blazer with a midi pencil skirt is a chic business casual winter outfit.
Sweater Dress Worn as a Pencil Skirt – Tuck in a sweater dress for a creative take on a winter pencil skirt outfit.
Fitted Turtleneck with Statement Belt Over Pencil Skirt – Define your waist with a statement belt over a turtleneck and pencil skirt combination.
Fluffy Cardigan and Ribbed Pencil Skirt – Add a touch of softness with a fluffy cardigan over a ribbed pencil skirt.
Leather Jacket and Plaid Pencil Skirt – Give your outfit an edgy vibe by pairing a leather jacket with a plaid pencil skirt.
Cropped Sweater with a High-Waisted Pencil Skirt – Balance a cropped sweater with a high-waisted skirt for a stylish winter look.
Winter White Pencil Skirt and Turtleneck Combo – Opt for a winter white outfit with a white pencil skirt and turtleneck for a fresh, snowy aesthetic.
Pencil Skirt with a Statement Scarf – Add warmth and style by draping a bold statement scarf over your outfit.
Oversized Blazer with a Knit Pencil Skirt – Wear an oversized blazer with a knit pencil skirt for a trendy winter office look.
Layered Poncho Over a Pencil Skirt – Stay extra cozy by layering a poncho over a fitted pencil skirt outfit.
Sweater Vest Over a Button-Down Shirt with Pencil Skirt – Add sophistication by layering a sweater vest over a classic button-down.
Quilted Jacket and Wool Pencil Skirt – Keep warm with a quilted jacket paired with a wool pencil skirt.
Winter Pencil Skirt Outfit with Faux Suede Boots – Pair a winter pencil skirt with faux suede boots for a stylish cold-weather look.
Longline Cardigan Over a Fitted Pencil Skirt – Add warmth without bulk by layering a longline cardigan over a fitted skirt.
Fitted Blazer and Knee-High Boots with a Pencil Skirt – A fitted blazer with knee-high boots makes for an ultra-chic winter ensemble.
Pencil Skirt with a Knit Turtleneck Dress as a Top – Repurpose a knit dress by tucking it into your pencil skirt.
Sweater with a Front Slit Pencil Skirt – Show off a hint of leg with a front slit pencil skirt paired with a cozy sweater.
Winter Pencil Skirt Outfit with Faux Fur Stole – Elevate your look with a luxurious faux fur stole over your outfit.
Hooded Coat and Thick Knit Pencil Skirt – Stay warm by layering a hooded coat over a thick knit pencil skirt.
Button-Down Shirt with a Knitted Pencil Skirt – A crisp button-down shirt looks stylish with a knitted pencil skirt.
Pencil Skirt with an Asymmetrical Sweater – Add flair with an asymmetrical sweater paired with a classic pencil skirt.
Layered Tights and Heeled Ankle Boots with a Pencil Skirt – Keep warm and stylish with layered tights and ankle boots.
Tweed Pencil Skirt with a Knit Turtleneck – Go for a classic look with a tweed pencil skirt and a warm turtleneck.
Winter Pencil Skirt Outfit with a Wool Beret – Complete your winter outfit with a chic wool beret.
Sweater Dress Over a Pencil Skirt – Get creative by layering a sweater dress over a pencil skirt.
Patterned Tights with a Solid Pencil Skirt – Add a fun touch with patterned tights under a solid-colored pencil skirt.
Shearling Coat with a Midi Pencil Skirt – Stay warm with a cozy shearling coat over your pencil skirt outfit.
Turtleneck with an Embellished Pencil Skirt – Go for a festive look with an embellished pencil skirt and a warm turtleneck.
Winter Pencil Skirt Outfit with Layered Camisole and Sweater – Layer a camisole under a sweater for extra warmth.
Belted Blazer and Velvet Pencil Skirt – Define your silhouette with a belted blazer over a velvet pencil skirt.
Pencil Skirt with a Cozy Hoodie and Coat – Dress down your pencil skirt with a cozy hoodie and structured coat.
Layered Knitwear with a Wool Pencil Skirt – Wear layered knitwear with a wool pencil skirt for extra warmth.
Pleated Pencil Skirt with a Chunky Sweater – Add movement to your look with a pleated pencil skirt.
Oversized Scarf Over a Pencil Skirt Outfit – Keep warm with an oversized scarf over your winter pencil skirt outfit.
Quilted Vest with a Midi Pencil Skirt – Layer a quilted vest over a long-sleeved top and pencil skirt.
Pencil Skirt with a High-Neck Sweater and Statement Earrings – Dress up your outfit with statement earrings.
These 50+ winter pencil skirt outfit ideas will keep you stylish and cozy all season long!
Hi, I’m Victoria Cook, the proud creator behind EverOutfits.com. As a dedicated mom and fashion enthusiast, I’ve always believed that the right outfit can make a world of difference, not only in how you look but also in how you feel. From juggling the demands of motherhood to managing everyday life, I understand the importance of finding outfits that are not only stylish but also practical and comfortable.