Skirts can be challenging to wear in winter but with a bit of planning and enough layering, learning how to wear skirts in winter can make a huge difference on how you present yourself to the world when the weather turns dark and cold.
The following looks are some of the many pieces that you can purchase from Mytheresa´s online store. I picked these particular looks because with just a few tweaks, you can easily re-create these looks as your own this winter. The tweaks that you may need to do includes adding leggings, tights or stockings to keep your legs warm, or swapping open-toe shoes for some warm, winter boots.
I will also try to suggest cheaper alternatives to these beautiful fashion pieces featured here because not all of us are able or willing to splurge on everything designer.
Table of Contents
1. How to wear skirts in winter: long skirts
If you´re aiming for maximum coverage and warmth when wearing skirts, thick, long A-line skirts in wool are absolutely perfect for you. The A-line silhouette gives you enough room to wear tall boots with.
A. Long wool coat on a long linen skirt
If you can find a long A-line skirt in wool, it´s better. However, a long skirt in linen will work too. Notice that it´s the pairing together of dark earthy tones that makes this winter look coveted.
Pair a dark gray sweater with the long olive green A-line skirt, add a a dark brown wool coat, and finish up with tall black leather boots.
B. Shearling coat on a suede long skirt and suede tall boots
Pairing a suede long skirt with suede tall boots is another way to wear long skirts in winter. To play up the length, add a long shearling coat as well. Notice how it´s only the skirt that´s in dark color. It allows the skirt to take center stage without overwhelming the look with black.
Just a heads up for petites, this outfit can easily overwhelm your small frame. So be careful.
2. How to wear skirts in winter: midi skirts
There are many styles of midi skirts that you can wear in winter. In fact, any midi skirt you wear in summer can be worn in winter. It´s simply all about layering it with warm, thermal leggings or tights to keep your legs warm.
A. Colored bomber jacket on a bright gathered midi skirt
If you have a skirt with mermaid shape, you can wear it with a turtleneck sweater, a thick bomber jacket or cropped parka jacket, some black tights, and pointed-toe black ankle boots.
B. Checked coat and denim midi skirt
For a casual winter look, style your midi denim skirt with a white turtleneck ribcage sweater, an oversized and long checked coat, and some cowboy-inspired boots.
C. Long wool coat with plaid midi skirt
There are times when you wonder how to wear skirts in winter for formal or business gatherings. Well, why not dress up your favorite midi pencil skirt? If it has that classy plaid print, all the better.
Let your skirt be the center of attention by wearing it with all black—a black turtleneck top or sweater, a black long top coat, ideally with hems that hit just an inch above your skirt or an inch longer than your skirt, black tights, and black knee-high leather boots.
D. A shearling jacket with wrap midi skirt and boots
Even wrap midi skirts can be worn in winter. To mimic this look above, simply swap the white top with a white cashmere sweater, layer the wrap floral print midi skirt with black tights, keep the black edgy ankle boots, and add a leather jacket or a cropped fur jacket to keep things warm.
A dark teal jacket looks fabulous in this look, but you can always opt for a black jacket instead.
E. A puffer coat over white denim midi skirt
An all white outfit may look too delicate for winter but not if you add a really cozy puffer coat.
Here, we see a white midi skirt worn with a sweater and some tall white boots. Adding not just any puffer coat but a colored one that grabs attention, is key to making your white outfit looks exciting for winter.
So if you wanted to know how to wear white midi skirt in winter, this is it!
3. How to wear skirts in winter: maxi skirts
Skirts may provide more versatility to wear in winter because you can mix and match, but it functions just like a dress. It only works if you layer it with thermal undergarments.
A. Hooded jacket with maxi skirt and combat boots
This is how to wear a tutu skirt casually in winter. Add a fitting gray pullover, a gray hodded jacket, some beige leggings, and black combat boots.
B. Quilted down coat with maxi skirt and flat ankle boots
Midi skirts are fun to wear in summer, but they can be equally just as fun in winter. Try the pleated midi skirt with a warm, turtleneck sweater, a black, belted parka coat, and some black combat boots.
The cascading hem of your skirt that peaks beneath your parka will keep a dull and boring look at arms length because parka doesn´t have to be boring.
C. A Black coat on a black maxi skirt
If you admire Angelina Jolie´s minimalism, this outfit is perfect to mimic. It´s all black, so what´s there to love?
Well, other than you´re layering a black on many blacks, the femininity of your pleated black midi skirt is what stands out in this look. Keep it edgy yet still feminine.
4. How to wear mini skirts in winter
Mini skirts are sort of challenging to wear in winter because unless you layer them with really thick leggings or tights, it´s almost impossible to survive a really cold winter day even if you wear it with a long wool or robust parka coat.
A. Wool coat on a wool mini skirt
If you´re wearing your mini skirt to a party, you drive to the party in a car, you get out the car and go inside a building, you really don´t need a pair a thick tights. You´ll be fine with just a pair of opaque stockings, right?
So go ahead and match your mini skirt with a fabulous button-down shirt, preferably with gold buttons. Bring out those super sexy tall suede boots with stiletto heels. And wrap yourself with a long, black top coat.
B. Twill raincoat on a vintage check wool mini skirt
Beige remains strong even in winter. If you have the classic designer plaid mini skirt, wear it with a black top and a beige coat. Match your tall boots and bag with your top.
C. Canvas jacket with skort and sneakers
This look on the model is suited for fall or spring. However, you can mimic it for winter too. Depending on how cold winter is on your side of the world, you can add some beige or brown tights and a really thick scarf on your neck to keep yourself warm outdoor.
5. How to wear knee length skirts in winter
Knee length skirt is probably the most versatile skirt to wear in winter. It gives you more options for your shoes—boots, flats, or sneakers.
A. Short parka jacket on a quilted high-rise skirt
Lets start with the quilted knee length skirt. It looks great with a cropped parka jacket and some platform leather boots. This look may seem very basic, somewhat dull, but you can always spice it up with an attractive long shawl.
B. Bright puffer coat to match a bright print midi skirt
Keep things bright this winter. Yeah, why not?
If you have a bright printed knee length skirt, you can easily wear it with a bright puffer coat, or any bright oversized coat, and everythings else in the look is black.
C. Double-breasted down coat with knee length skirt and sneakers

That sexy assymetrical hem, knee length skirt that you wore with high heels in summer? You can also wear it with some sneakers, a simple top, and your powerful long parka for a casual look this winter. A beige top is great to match your beige print sneakers. But really, you can opt for bright colors for this look as well.
D. Wool and cashmere cardigan with leather knee length skirt and boots
And this is how you wear a leather knee length skirt in winter. Wear it with any of your favorite sweaters and add some interesting leather shoes. Because it´s the contrast of leather and knits that will make your outfit interesting and attractive.
There you have it, these are the many outfit ideas on how to wear skirts in winter. Remember, skirts can be your key fashion staple in winter so long as you have no problem wearing tights or leggings with them.