13 Trendy Winter Skirt Outfits That’ll Keep You Warm and Stylish

As the temperatures drop, you might be tempted to pack away your skirts until spring. But don’t put them in storage just yet! Winter skirt outfits can be both stylish and cozy when paired with the right pieces. From mini skirts with tights to maxi skirts with boots, there are so many ways to rock a skirt even in the coldest months.

In this post, I’ll share 13 trendy winter skirt outfits that’ll keep you looking chic while staying warm. You’ll find ideas for casual everyday looks, office-appropriate ensembles, and even some dressier options for nights out. The key is layering – think chunky sweaters, warm tights, and knee-high boots. With the right combinations, you can wear your favorite skirts all year round.

So, if you’re looking for fresh winter outfit inspiration, keep scrolling! These looks will have you excited to style your skirts even when there’s snow on the ground. Let’s explore these cozy yet fashionable winter skirt outfit ideas.

Winter Skirt Outfit Ideas

1. Casual Cool: Denim Mini Skirt and Chunky Knits

Casual Cool: Denim Mini Skirt and Chunky Knits

Create an effortlessly cool winter look by combining a blue denim mini skirt with cozy knits. Opt for a ribbed sweater in a neutral tone like cream or gray, and layer on a chunky knit scarf in a coordinating color for extra warmth.

To keep your legs warm, add a pair of thick tights or knee-high socks. Brown ankle boots complete the outfit perfectly. I love how ankle boots hit at just the right spot with a mini skirt, elongating your legs.

A black crossbody bag adds a practical touch while keeping your hands free. This ensemble is ideal for weekend errands or grabbing coffee with friends. The mix of textures between the denim, knits, and leather creates visual interest while still feeling cozy.

2. Sleek and Chic: Turtleneck and Maxi Skirt

Sleek and Chic: Turtleneck and Maxi Skirt

For a more polished winter look, consider pairing a fitted turtleneck with a long maxi skirt. The combination of a white plaid turtleneck top with a dark maxi skirt creates an eye-catching yet sophisticated contrast.

To keep this outfit winter-appropriate, add a pair of knee-high boots. Not only will they keep your legs warm, but they also add a touch of drama peeking out from under the long skirt. You might love trying this look for the office or a nice dinner out.

The long lines of the maxi skirt and tall boots create a sleek silhouette that’s both elegant and cozy. It’s a great way to stay warm without sacrificing style.

3. Romantic Flair: Puff Sleeves and Midi Skirt

Romantic Flair: Puff Sleeves and Midi Skirt

Add some romantic flair to your winter wardrobe with this pretty combination. A black puff-sleeve top adds a feminine touch, while a burgundy midi skirt introduces a rich, seasonal color palette.

Black knee-high boots keep the look winter-appropriate and streamlined. For an extra style statement, top it off with a black newsboy cap. This trendy accessory adds a bit of vintage charm to the outfit.

The balance between romantic elements like the puff sleeves and midi skirt with edgier pieces like the boots and cap makes this ensemble perfect for a date night or girls’ night out in the colder months.

4. Classic with an Edge: Leather Mini and Camel Coat

Classic with an Edge: Leather Mini and Camel Coat

Combine classic and edgy elements with this stylish winter outfit. A timeless camel coat serves as the perfect backdrop for a white turtleneck sweater and a black leather mini skirt.

The contrast of the structured coat with the edgy skirt creates a cool juxtaposition. Black tights keep your legs warm, while black combat boots add a touch of grunge.

This combination works well for those days when you want to look put-together but still a bit rebellious. It’s one of my favorite looks for its mix of classic and edgy elements.

5. Cozy Chic: Striped Sweater and Ribbed Maxi

Cozy Chic: Striped Sweater and Ribbed Maxi

When comfort is key but style is still important, reach for this cozy outfit. Pair a striped sweater with a ribbed maxi skirt in a coordinating color. The key to making this look work for winter is in the texture – the ribbed fabric of both pieces adds visual interest and extra warmth.

Knee-high boots complete the look perfectly. This ensemble is ideal for lazy weekend days when you want to be comfortable but still look put-together enough to run errands.

The long maxi skirt provides coverage and warmth, while the fitted sweater keeps the silhouette from looking bulky.

6. Boho Winter: Turtleneck and Floral Maxi

Boho Winter: Turtleneck and Floral Maxi

Bring some boho vibes to your winter wardrobe with this pretty combination. Begin with a black turtleneck sweater as your base layer. Then, add a floral print maxi skirt for a pop of color and pattern.

To winterize this look, pair it with black knee-high boots. The tall boots not only keep you warm but also add a sleek element to balance out the flowing skirt. You might love trying this outfit for a winter brunch or a casual day at the office.

This outfit combines the coziness of a sweater with the free-spirited feel of a floral maxi skirt, making it great for a winter brunch or a casual day at the office.

7. Bold and Bright: Oversized Coat and Sweater Dress

Bold and Bright: Oversized Coat and Sweater Dress

When the winter blues hit, sometimes you need to brighten things up with your outfit. Try this bold look featuring a bright oversized coat paired with an equally vibrant turtleneck sweater dress.

To keep the focus on the colorful top half, add some black over-the-knee boots. These sleek boots balance out the volume of the coat and keep your legs warm. Finish off the look with some cat-eye sunglasses for a touch of retro glam.

This outfit is perfect for those gray winter days when you need a pop of color to lift your spirits. The oversized coat and sweater dress combo is not only on-trend but also super cozy.

8. Preppy Cool: Sweatshirt and Plaid Mini

Preppy Cool: Sweatshirt and Plaid Mini

Channel a cool, preppy-inspired winter look with this combination. A black sweatshirt provides a casual, comfortable base, while a plaid mini skirt adds a classic schoolgirl vibe.

Black tights and lace-up boots make the outfit winter-appropriate and add a bit of edge to balance out the preppy elements.

This look takes classic preppy pieces and gives them a cool, modern twist, perfect for a casual day out or even a laid-back office environment.

9. Layered Textures: Ribbed Sweater and Plaid Mini

Layered Textures: Ribbed Sweater and Plaid Mini

Play with textures and proportions in this stylish winter outfit. Combine a light-colored ribbed sweater with a dark plaid mini pencil skirt for a classic winter pattern.

Black knee-high socks create a cool layered look when paired with black combat boots. A black crossbody bag adds a practical touch to finish the ensemble.

The mix of the cozy sweater, structured skirt, and edgy boots creates a balanced and interesting outfit, ideal for a day of shopping or meeting friends for coffee.

10. Sleek Monochrome: Crop Sweater and Maxi Skirt

Sleek Monochrome: Crop Sweater and Maxi Skirt

For a sleek, monochromatic winter look, try this all-black ensemble. Start with a black turtleneck crop sweater – the cropped length adds a modern touch. Pair it with a black maxi skirt with a side slit detail for a hint of drama.

To add some contrast and keep warm, layer some black tights underneath. Then, surprise everyone with a pair of white chunky lace-up boots. These boots add a cool, unexpected element to the all-black outfit.

I love how this outfit plays with proportions – the cropped sweater and long skirt create an interesting silhouette. It’s perfect for a night out or any event where you want to make a stylish statement.

11. Sweet and Feminine: Lace Collar and Midi Skirt

Sweet and Feminine: Lace Collar and Midi Skirt

Embrace a sweet, feminine winter look with this pretty combination. A white turtleneck sweater with a lace collar detail adds a delicate touch to a winter staple, while a gray ribbed midi skirt creates a soft, tonal look.

Black sheer tights add warmth and a bit of texture, and black ankle boots keep the look winter-appropriate. A black shoulder bag provides a practical finishing touch.

The mix of textures – from the lace collar to the ribbed skirt – adds interest to the simple color palette, making it perfect for days when you want to feel put-together and pretty, even in the depths of winter.

12. Office Chic: Blazer and Geometric Skirt

Office Chic: Blazer and Geometric Skirt

Create a work-appropriate winter outfit that doesn’t sacrifice style with this combination. Layer a black turtleneck top under a black blazer for a polished, professional base.

Add personality with a multicolored geometric print skirt, bringing interest to the otherwise simple outfit.

Black tights, pointed-toe shoes, and a structured black handbag complete the look. This ensemble works well for the office or any professional setting where you want to look put-together but still show some personality.

13. Boho Layers: Leather Jacket and Tiered Maxi

Boho Layers: Leather Jacket and Tiered Maxi

For a boho-inspired winter look with an edge, try this layered outfit. Combine a striped top with a dark leather jacket for some rock ‘n’ roll attitude. A tiered maxi skirt provides a flowing silhouette that contrasts nicely with the structured jacket.

Ankle boots keep the look winter-appropriate, while a wide-brim hat adds extra boho flair. This outfit is ideal for a concert or a night out when you want to channel your inner free spirit, even in the cold weather.

The combination of different styles – the edgy leather jacket, the bohemian maxi skirt, and the classic striped top – creates a unique and stylish look.

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