Who said skirts are just for summer? I’m here to prove that you can totally rock your favorite skirts even when it’s freezing outside.
The secret is all in the layering. Think cozy knits, warm tights, and the perfect pair of boots.
Get ready to screenshot these looks, because they’re about to become your new winter uniform.
1. Preppy Cool: Sweatshirt and Plaid Mini
I am always here for an outfit that finds that perfect sweet spot between comfortable and cool. This combination is such a home run.
Start with a black sweatshirt for a casual and comfy base, then pair it with a plaid mini skirt. It gives off that classic schoolgirl vibe that’s so on-trend right now.
To make it completely ready for winter, just add some black tights and a pair of lace-up boots.
I love how these pieces give the whole look a little bit of an edge, which keeps the preppy style feeling modern and fresh.
This is one of those outfits that’s perfect for a casual day out or even a super laid-back office setting.
2. Romantic Flair: Puff Sleeves and Midi Skirt
Seriously, how perfect is this look for a date night or a fun girls’ night out during the colder months? It has such a romantic feel.
The black puff-sleeve top is so feminine, and pairing it with a burgundy midi skirt brings in such a rich, seasonal color. It’s just gorgeous.
Black knee-high boots make the whole outfit feel streamlined and totally winter-appropriate. And the black newsboy cap? That’s the finishing touch that I’m obsessed with.
It’s a trendy accessory that adds a little bit of vintage charm. I just love the mix of romantic details and slightly edgier pieces.
3. Sweet and Feminine: Lace Collar and Midi Skirt
Sometimes you just want an outfit that feels pretty and completely put-together, you know? This look absolutely nails that vibe.
A white turtleneck sweater is already a winter staple, but the delicate lace collar detail makes it feel so special. Paired with a gray ribbed midi skirt, it creates this soft, tonal look that’s so beautiful.
Add some black sheer tights for warmth and a touch of texture. Black ankle boots are the perfect shoe choice to keep it ready for the season.
A simple black shoulder bag is all you need to finish it off. The mix of textures is what really makes this outfit a standout, making it perfect for those days you want to feel pretty, even when it’s freezing outside.
4. Casual Cool: Denim Mini Skirt and Chunky Knits
For a winter look that feels totally cool without even trying, this is your new go-to. I love combining a blue denim mini skirt with some really cozy knits.
Just grab a ribbed sweater in a neutral color like cream or gray, and then layer on a chunky knit scarf in a color that coordinates. It’s an instant recipe for extra warmth.
To keep your legs from freezing, a pair of thick tights or even some knee-high socks will do the trick. Brown ankle boots are the perfect finishing touch here.
I personally think ankle boots hit at just the right spot with a mini skirt to make your legs look longer.
A black crossbody bag is a practical choice that also keeps your hands free. This whole vibe is just ideal for weekend errands or meeting up with friends for coffee.
The blend of textures from the denim, knits, and leather is what makes it so visually interesting while still being super cozy.
5. Cozy Chic: Striped Sweater and Ribbed Maxi
On those days when comfort is the number one priority but you still want to look stylish, this outfit is the answer. Pairing a striped sweater with a ribbed maxi skirt in a similar color is such a great move.
The real key to making this work for winter is all about the texture; the ribbed fabric on both pieces adds so much visual interest and a little extra warmth.
Knee-high boots are the perfect shoe to complete this look. I can totally see myself wearing this for a lazy weekend day when I want to be comfortable but also look put-together enough to go run some errands.
The long maxi skirt gives you plenty of coverage and warmth, and since the sweater is more fitted, the whole silhouette doesn’t look bulky at all.
6. Office Chic: Blazer and Geometric Skirt
Putting together a winter outfit for work that doesn’t feel boring can be a challenge, but this combo is a total win. Layering a black turtleneck top under a black blazer creates such a polished and professional base to start with. It’s a classic for a reason!
This is where you can add some personality. A multicolored geometric print skirt brings so much interest to what is otherwise a pretty simple outfit.
From there, all you need are some black tights, pointed-toe shoes, and a structured black handbag to complete the look.
This ensemble is perfect for the office or any professional setting where you want to look sharp but still show off your personal style.
7. Sleek Monochrome: Crop Sweater and Maxi Skirt
If you’re going for a sleek, monochromatic winter outfit, you have to try this all-black look. It’s so good. Start with a black turtleneck crop sweater; I love how the cropped length gives it a modern feel.
Then, pair that with a black maxi skirt that has a side slit detail for just a little bit of drama.
To add some contrast and, more importantly, to stay warm, layer a pair of black tights underneath. And for the shoes, here’s the fun part: a pair of white chunky lace-up boots!
They add such a cool and unexpected pop to the all-black outfit. I’m obsessed with how this look plays with proportions.
It’s a great choice for a night out or any event where you want to make a seriously stylish statement.
8. Bold and Bright: Oversized Coat and Sweater Dress
When those winter blues start to creep in, sometimes the best thing to do is fight back with a super bright outfit. This bold look is perfect for that.
It features a bright oversized coat paired with a turtleneck sweater dress that’s just as vibrant. It’s impossible not to feel cheerful in these colors.
To keep all the attention on the colorful top half, add a pair of black over-the-knee boots. These boots are so sleek, and they really balance out the volume from the coat while also keeping your legs nice and warm.
For a final touch, add some cat-eye sunglasses for a little bit of retro glam. This outfit is not only on-trend but also incredibly cozy.
9. Sleek and Chic: Turtleneck and Maxi Skirt
For a winter look that’s a bit more polished, I love the idea of pairing a fitted turtleneck with a long maxi skirt.
The combination of a white plaid turtleneck top with a dark maxi skirt creates such a sophisticated contrast that really catches the eye.
To make this outfit work for winter, knee-high boots are a must. Not only do they keep your legs warm, but I think they add a touch of drama when they peek out from under the long skirt.
I could totally see this being a great look for the office or for a nice dinner out. The long lines of the skirt and boots create a silhouette that’s both elegant and cozy.
It’s a perfect way to stay warm without giving up on style.
10. Boho Layers: Leather Jacket and Tiered Maxi
If you’re looking for a boho-inspired winter outfit with a little more edge, you have to try this layered look. Combining a striped top with a dark leather jacket gives it some of that rock ‘n’ roll attitude.
Then, a tiered maxi skirt adds a flowing silhouette that creates a really nice contrast with the structured jacket.
Ankle boots will keep the look winter-appropriate, and a wide-brim hat is perfect for some extra boho flair. This is such a great outfit for a concert or a night out when you want to channel your inner free spirit, even when it’s cold outside.
The mix of different styles—the edgy jacket, the bohemian skirt, and the classic top—comes together to create a look that’s so unique and stylish.
11. Classic with an Edge: Leather Mini and Camel Coat
I am a huge fan of mixing classic and edgy pieces together, and this winter outfit does it perfectly. A timeless camel coat is the perfect backdrop for a simple white turtleneck sweater and a black leather mini skirt.
The contrast between the structured coat and the edgy skirt creates such a cool juxtaposition. Black tights are a must for keeping your legs warm, and a pair of black combat boots adds just the right touch of grunge.
This combination is one of my favorites. It’s ideal for those days when you want to look put-together but still feel a little bit rebellious.
12. Boho Winter: Turtleneck and Floral Maxi
You can totally bring some boho vibes into your winter wardrobe with this pretty combination. Just start with a black turtleneck sweater as your base layer, which is always a good idea.
Then, add a floral print maxi skirt for a pop of color and pattern that feels so cheerful.
To make this look ready for winter, all you need is a pair of black knee-high boots. The tall boots are great for staying warm, but they also add a sleek element that balances out the flowing skirt.
I would absolutely wear this for a winter brunch or even a casual day at the office. It combines the coziness of a sweater with the free-spirited feel of a floral skirt perfectly.
13. Layered Textures: Ribbed Sweater and Plaid Mini
Playing with different textures and proportions is such a fun way to build a stylish winter outfit. This look is a perfect example.
Combine a light-colored ribbed sweater with a dark plaid mini pencil skirt for that classic winter pattern we all love.
Now for the layers. Black knee-high socks paired with black combat boots create a really cool layered effect. A simple black crossbody bag is a practical touch that finishes the whole look.
The mix of the cozy sweater, the structured skirt, and the edgy boots creates an outfit that feels balanced and interesting. It’s ideal for a day of shopping or meeting up with friends for coffee.