Cozy Chic Winter Skirt Outfit Ideas
Skirts don’t have to disappear into the back of your closet as soon as winter hits.
There are so many cute ways to wear them when it’s cold, whether you’re styling a mini skirt with tights and boots or throwing on a long skirt with your favorite sweater.
I put together some of my favorite winter skirt outfit ideas below with a mix of casual, dressy, and work-friendly looks you can easily copy.
Plaid Maxi Skirt + Leather Jacket
Plaid skirts are always cute for winter, and I love this longer maxi style with brown boots. Pair it with a simple white top and throw an oversized leather jacket over it for an easy casual outfit.
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You could also wear this with a chunky sweater or swap the fringe boots for a simple pair of knee-high boots. Add your favorite everyday bag and you’re good to go.
Mini Skirt + Gray Sweater
This is such an easy way to wear a mini skirt in winter without feeling too dressed up. Layer a white button-down under an oversized gray sweater and add a simple black mini skirt.
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The lace tights are really cute here, but regular sheer or black tights would work too. Finish it off with chunky black boots and a fun bag for a little pop of color.
Navy Maxi Skirt + Plaid Coat
A long navy skirt is a great option if you need something a little more dressed up for work or dinner. Wear it with a simple navy sweater and add a long plaid coat on top.
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The printed heels are fun here, but you could easily make this more casual with loafers or boots. A black or brown bag would work with it too.
Burgundy Satin Skirt + Cardigan
Burgundy is such a pretty color for winter, and this outfit would be perfect for a date night or holiday party. Pair a satin midi skirt with a cute cropped cardigan and matching heels.
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You definitely don’t have to match everything either. A cream sweater or black cardigan would look just as cute with a burgundy skirt if you want to use pieces you already have.
Black Maxi Skirt + Turtleneck
You really can’t go wrong with an all black outfit, especially when you want something easy that still looks dressed up. Pair a long black skirt with a fitted or cropped turtleneck and simple flats.
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This would also look cute with boots if it’s too cold for flats. Throw on a long coat and add a small shoulder bag for an easy winter dinner outfit.
Leather Mini Skirt + Plaid Blazer
A black mini skirt with tights is one of those outfits you can wear so many different ways all winter. This leather one looks really cute with a black turtleneck and oversized plaid blazer.
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Add chunky loafers and socks for a more preppy look, or wear it with boots if that’s more your style. You could also swap the leather skirt for a basic black mini and get almost the exact same look.
Black Lace Skirt + Denim Jacket
A lace skirt doesn’t have to be saved for a fancy outfit. Wear it with a simple black top, oversized denim jacket, and tall boots to make it feel way more casual.
I really like the all black look here, but you could also do this with a regular blue denim jacket. This would be cute for dinner or drinks when you want to wear something a little more fun than jeans.
Burgundy Mini Skirt + Matching Jacket
Here’s another cute way to wear burgundy this winter. A matching mini skirt and jacket makes getting dressed really easy, and you don’t need to add much else to make the outfit feel complete.
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The printed tights are such a fun addition, especially with a shorter skirt. Add heels for a dressier look or swap them for loafers or boots to make it a little more casual.
Polka Dot Skirt + Brown Sweater
A printed midi skirt is an easy way to switch things up if you’re getting bored with plain winter outfits. Pair a brown polka dot skirt with a cozy sweater, tall boots, and a long coat.
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I love all the different shades of brown together here, but you don’t need everything to match. A cream sweater or black coat would work just as well with this skirt.
Plaid Mini Skirt + Fair Isle Sweater
This is such a cute classic winter outfit and really easy to recreate. Layer a Fair Isle sweater over a white button-down and pair it with a plaid mini skirt and black tights.
Add chunky loafers and socks like she did here, or just wear your favorite black boots. You could also skip the button-down underneath if you want to keep the outfit a little simpler.
Leopard Skirt + Black Blazer
Leopard skirts are back in a big way, and this is such an easy way to wear one without making the outfit feel over the top. Pair it with a basic white tee, oversized black blazer, and ballet flats.
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The red shoes are really cute if you want to add some color, but black flats would work just as well. When it gets colder, swap the t-shirt for a long sleeve top or sweater and add tights.
Black Maxi Skirt + Sneakers
This is probably one of the easiest winter skirt outfits to actually wear on a normal day. Pair a simple black maxi skirt with a striped cardigan and your favorite sneakers.
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Add a shoulder bag and a few simple accessories and that’s really all you need. You could also throw a jacket or long coat over this when it gets colder.
Black Lace Skirt + Sweater
A black lace skirt is such a fun piece to have in your closet because you can dress it up or down. I love it here with the oversized blue sweater and flats for a cute winter outfit that still feels really easy to wear.
Throw a leather jacket over it when you need another layer, or swap the flats for boots on colder days. You could also recreate this with a plain black skirt if lace isn’t your thing.
Gray Mini Skirt + Mary Janes
A gray mini skirt is another really easy piece to style for winter. Pair it with an oversized gray sweater and Mary Janes for a simple outfit that still feels cute and trendy.
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Wear it with socks on a warmer day or add black tights when it’s actually cold out. You could also swap the Mary Janes for loafers or boots and throw a long coat on top.
How to Wear Skirts in Winter
You really don’t need to buy a bunch of new skirts just for winter. Most of the skirts already in your closet can work when you pair them with sweaters, tights, boots, and heavier jackets.
Mini skirts are easy to wear with tights and boots or loafers, while midi and maxi skirts look cute with everything from sneakers to tall boots. I also love throwing a long coat over a skirt outfit when it’s really cold because you still get the cute outfit once the coat comes off.
And don’t be afraid to wear some of your dressier skirts during the day. Satin and lace skirts can look really cute with an oversized sweater, sneakers, or a casual jacket and give you another way to wear pieces that might otherwise just sit in your closet.
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