Adding winter skirt outfits to my rotation during these chilly months has been a game-changer for me this year! Planning winter outfits can feel so boring when it feels like your only options are pants, and nothing else.

Who said you have to tuck away all of your mini and midi skirts with your summer attire? With all kinds of options like over the knee boots and fleece-lined tights, we have no excuse to pretend that we can’t wear skirts this season.

Get creative and brave with those skirts with me!

There are tons of ways to still wear them in the winter, and I’m going to show you just how to do it.

Dress up your winter wardrobe with some of these ideas.

Four girls wearing cute outfits for winter.

I always struggle to look put together in the winter because my natural bent is to get cozy and stay cozy until the sun comes back to warm us up.

Here are some ideas for wearing a skirt in every season so you can visualize just how versatile your skirts really are!

Pro Tip: Pair every skirt with a chunky sweater and heels for an immediate cozy chic vibe.

A girl standing by a neon sign wearing a skirt with tights.

With Tights

Building an outfit around a skirt while it’s cold outside usually ends up involving a good pair of tights.

I don’t mind wearing subtle and skin toned ones or opt for bright tights and add a statement to the outfit.

1. Monochrome

An all black layered outfit is the classiest go-to.

2. Contrast

A dark tight with a lighter outfit brings a wintery look to a brighter color palette. Contrast plays a huge part in the overall look of the outfit.

3. Funky Addition

If you need a little something fun and funky for your outfit, I love this combo of polka dots with the tennis skirt.

4. Patterned Up

Pairing two classic patterns can add an element of fun to an outfit of staples. This cable knit and plaid combo is soft but still so interesting.

5. Lace Tights

Get playful in a solid outfit with some lace tights!

6. Sheer Black

Sheer black tights are a great throw on, even under a hot pink skirt.

7. Neutrals

It doesn’t get more classic for the winter than this: black sweater, brown skirt, and black tights.

8. Fun In Fishnets

‘Tis the season for some iconic layers, and this fishnet outfit is just the perfect examples of using certain pieces can level up a whole look.

Three girls wearing leather winter outfits.


Leather skirts turn what could be a pretty girly look to something with a little bit of edge. Leather bottoms are becoming as much as a staple as denim is, purely because of how many ways you can wear it!

Check out these leather skirt outfit ideas.

9. Side Zipper Skirt

This side zipper leather skirt is the cutest basic to have in your wardrobe to pair with any sweater or jacket.

10. Pleated Skirt

A pleated leather mini adds a little flare to everything.

11. Cutie Stripes

A combination like this makes the leather a little more palatable for those that aren’t looking for a super edgy look. A soft and easy pattern like stripes accomplishes this look.

12. Matching Puffer Jacket

I love this look! A cropped leather puffer jacket is one of my closet staples for winter, and adding in a leather mini skirt to make it a whole outfit is ideal for the winter weather.

13. Fitted Top

A fitted top is the go-to pairing with a leather mini skirt.

14. Super Styled

If you’re not worried about the bitter winter winds, this is a great example of styling something for winter without actually bundling up. The vibes are there, even if the knits and layers aren’t! So cute.

15. Sweater Vest

A sweater vest is the easiest pull on for this kind of outfit.

Three women wearing trendy maxi skirts in different styles.

Maxi Skirts

I remember growing up these maxi skirts were so NOT it.

But just like everything else, they’ve come back around and changed my mind. These are huge this year, and if you haven’t yet you’ll want to hop on this trend.

They were originally a great summer piece but they transition really well into winter, for obvious reasons.

16. Dressed Down

This looks just as cozy as my favorite sweats, and I can get away with this just about anywhere!

17. Cargo And Bodysuit

This cargo skirt and bodysuit is a cool staple to use on rotation with your jeans outfits. And a green one like this changes it up from the denim looks too.

18. Moto Jacket

Throw on a moto jacket for the edge we all need with a maxi skirt.

19. Sneaker And Scarf

I love this contrast of cozy winter pieces and chunky casual shoes.

Tiered Skirt

A tiered maxi skirt in a neutral color might just be where you need to start to make this maxi skirt trend a statement in your closet. Easy to style and easier to wear! Comfortable and gorgeous at the same time!

20. Easy Monochrome

This is easily one of the most chic outfits in this roundup.

21. Turtleneck

Cover all the way up for a really fashion forward look this winter. This is the perfect example of doing the unexpected thing to get a really cool outfit.

22. Oversized Layers

An oversized sweater with a button-down peeking out the bottom is such a cute way to style these. Layers add intentionality, so even when it’s an oversized look, it works well together.

23. Cropped Sweater

An obvious choice is the cropped sweater, and with a cool sneaker you’ve got an effortlessly chic outfit.

24. Patterned Maxi

This patterned maxi brings so much character to every outfit.

25. Elegant Basics

Elevate your basics with this stunning pairing of blacks and whites.

26. Staple Denim

Convinced? Need a staple denim skirt? Here’s one of my favorites!

Three winter mini skirt outfits.

Mini Skirts

A mini skirt will always be a go-to to reach for when it comes time to get dressed, especially when your goal is to dress cute.

You don’t have to put them away for winter, just get some new ideas and inspiration including long socks – my current fav! Tights and boots are also easy wins here.

27. Plaid Neutrals

I love this easy neutral outfit based on layers to make it seasonally appropriate.

28. Classy Black Outfit

The perfect example of styling a mini skirt with all of the classiest pieces in your closet. A sweater over the shoulders is the perfect touch.

29. Blazer

Throw on a long-fitting blazer to make it look like dress layers.

30. Casual Pairings

This is a really cool pairing, with such an interesting skirt with a basic striped top. Keep it cool and casual with pieces that you don’t always expect.

31. Faux Leather

Snag a faux leather piece just to keep it fun.

32. Color Pop

Use the mini skirt as your source for a little color pop! This is so cute added to many layers of stark neutrals to make this so much cooler.

33. With A Puffer

Throw on a puffer jacket to balance it all out.

34. Pretty Oversized Knits

The loose and oversized sweater is perfect for this look. Be cozy and cool.

35. Total Turtleneck

The turtleneck is never going to not be a classic. Throw it on with anything for a beautiful look.

Two women in cute pencil skirts.

Pencil Skirts

Pencil skirts are the corporate style classic we love that are forever a piece in our closets for any occasion. So many fun styling ideas for the iconic pencil skirt, I want to wear more of these this season.

36. Wool

A chic and retro wool pencil skirt like this one is a statement piece all on its own.

37. Leather On Leather

This is a really edgy way to elevate your business attire that feels so corporate but can be something new and different after office hours.

38. Black On Black

Keep it classy!

39. Matching Set

So chic and so cute to wear as a matching set.

40. Base Layer

This denim pencil midi skirt makes the best base layer as you start to add the different textures, jackets, and knits to any outfit.

41. Cable Knit Sweater Skirt

Adding a sweater skirt to the mix is the ideal way to make this a winter look.

42. Matching Set

A matching set is the easiest way to look put together without trying very hard.

43. Neutrals

Add in a different kind of neutral with a brown vegan leather piece! This adds some dynamic to your outfit.

How To Wear A Skirt In The Winter

A winter skirt outfit feels a little counter productive, but if you’re willing to get a little creative, it’s an easy feat.
Of course tights and tall boots are great options when you need a little more coverage, and I always at least throw on a pair of nude tights just to help a little, but sometimes even just a little bit of balance makes it better.

If I know part of me is going to be pretty chilly, I can layer with a knit turtleneck under a sweatshirt or jacket that I’m planning to wear on top. And then throw on a pair of boots to make it even.

Don’t limit your look to a mini skirt!

This year, midi and maxi skirts are everywhere, so using one of these to cover up a little more and still get the skirt look is ideal for this season.

Winter skirt outfit ideas to put together for cold days like this pink-tiered maxi skirt.

This tiered tulle skirt look is the best for winter parties and more formal events.

Skirts shouldn’t be limited to the spring and summer seasons, wearing them along with your fall and winter wardrobes add an elevated sense of styling to your usual sweaters and jackets that we put on repeat all season long.

Don’t be afraid of layers and tall boots, they really come in handy when the wind hits and you need a little extra coverage.

Let the year’s trends like midis and maxis and tall boots play a part in how you’re rocking your winter wardrobe, and have fun bringing a skirt into the mix with me!

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