FASHION

How to Wear Skirts in Winter: Tips to Stay Warm and Look Stylish

A beautiful skirt can be the starting point for a very chic look, but when it’s freezing out, a skirt may be the last thing on your mind!  If you’re getting tired of always wearing pants, check out these tips on ways to wear a skirt in winter to look stylish and feel toasty.

 

How to Wear Skirts in Winter

How to Wear Skirts in Winter: Tips to Stay Warm and Look Stylish

1. Choose Heavier Fabrics So You are Not Sacrificing Warmth

When temperatures drop, you’ll want a skirt made of thicker, heavier fabrics. Think wool, tweed, weighty plaids, leather, suede, corduroy, and luxurious velvet. Knit skirts are perfect for bundling up. Lined skirts are also handy for fending off the cold, and skirts with a lot of fabric or layers can help keep you warm, too.

 

black winter skirt with boots

Leather pencil skirt

2. Slip on Tall Boots

Wearing tall boots with a winter skirt is practical and super chic. I love this look and find it’s the best way to keep my legs toasty. You can wear knee-high boots or even over-the-knee boots.  A very elegant look at the moment is tall boots tucked under the hem of a knee-length skirt, winter midi, or maxi with no skin showing.  Style tip:  When you wear boots that are the same color as your skirt, you will look taller.

 

gray plaid winter skirt

Houndstooth Skirt

3. Wear Tights or Leggings with Your Winter Skirt

Black, opaque, or semi-opaque tights layered under a skirt keep your legs warm and your outfit looking polished. Creative dressers may prefer colored or printed tights.  For super duper warmth, try fleece-lined tights or fleece leggings.

If you wear dainty shoes or have chunky legs, consider ultrasheer hose—black or nude to match your skin tone. Opaque stockings are thick and add visual weight, making heavy legs look heavier. Ultrasheer hoses are not as warm, but they’re better than bare legs in winter!

 

long purple satin skirt and cardigan

Satin skirt

4. Opt for a Longer Skirt

Wearing a midi or maxi skirt in winter keeps the goosebumps away!  Plus, longer lengths are very much on-trend this year.  Pair a long skirt with shoes or boots and add a cozy cardigan or fuzzy sweater on their own or with something underneath.

pink skirt layered

Confetti Plaid Skirt

5. Layer for Maximum Heat

If your top half is warm, you’ll keep the blood flowing, and the rest of your body will feel warm, too.  Layer using coats, scarves, sweaters, cardigans, vests, ponchos, and blazers to keep away the chill. Layering is also great because it makes your winter skirt outfit look more dimensional and interesting.

How to Style Skirts in Winter: Outfit Ideas to Copy

Styling Winter Skirt outfits is less of a style challenge than you think. Here are 5 ways to incorporate skirts into your wardrobe from December to March and stay warm!

brown suede winter circle skirt styled with sweater and boots

Suede Skirt

Suede Skirt with a Cropped Cableknit Sweater

A heavy fabric like suede looks right at home with a chunky sweater. And the cropped proportion is right on, too.  With a high-waisted skirt, you want to highlight your waist. A long, heavy sweater would add bulk to your stomach and hips and make you look frumpy and dated.

Add some booties and a bag in patent leather for a more 3D look.

camel wool a-line skirt

Camel Wool Skirt

Classic Wool Skirt with Tights and Loafers

So classy! Here’s that cropped sweater look again, this time with a classic camel, wool, A-line skirt. Is she wearing fleece tights with her skirt and loafers,  or isn’t she? They’re so good these days that you’d never know.

 

leather winter skirt and sweater

Leather A-line skirt

 

Leather A-line Skirt with Oversized Sweater and Tall Boots

Wow, this winter skirt outfit is a knockout! Edgy leather meets a bold pop of red. Notice how this fine cashmere sweater is oversized? Do a half tuck to give this outfit a relaxed, cool girl look. I love this with matching boots!

 

denim skirt leather jacket boots

Denim skirt| tee | Leather Jacket | Boots

 

Denim Midi Skirt with Leather Jacket and Suede Boots

For a more casual skirt look, this is a winner. I love this bell-shaped skirt paired with a long-sleeved tee and a gorgeous leather jacket. Tall suede booties add texture and a nice shot of color.

 

gray corduroy skirt | How to Wear Skirts in Winter

Corduroy skirt | top

Corduroy skirt with Sweater, Scarf and Booties

When it’s cold and wintry, nothing is cozier than a corduroy skirt. This cute outfit features shearling booties and a snuggly scarf over a sweatshirt.

 

winter skirt with ultrasheer hose and shoes

Satin skirt

 

Long Satin Skirt, Turtleneck Heels, and Stockings

Remember when I talked about wearing a semi-opaque or ultrasheer hose with finer shoes? Here’s an example. This look also works because the satin skirt is light and flowy, while thick opaque stockings would drag it down.
gray knit skirt and sweater | How to Wear Skirts in Winter

Sweater Skirt |Matching Sweater

Maxi Sweater Skirt, Knit Top

A sweater skirt is one of the coziest skirts you can wear in the winter.  I love it with this matching sweater and gray suede booties. So casually elegant!

wool winter pencil skirt and sweaterMaxi pencil skirt | sweater

Monochromatic Maxi Pencil Skirt and Sweater

This sleek green wool pencil skirt with a gorgeous cashmere sweater is pure class. This monochromatic color scheme is elegant and elongating. You can also wear this skirt with a turtleneck, cowl-neck sweater, or silky satin blouse.

The Final Word

Wearing skirts in winter is a great idea when you know all these stylish and cozy ways to wear them. I hope these tips have made it easier for you to create gorgeous winter skirt outfits.

If you’re a skirt girl at heart, all year round, not just in winter, you may also want to check out this related post on leather skirt outfit ideas!

Keep following along with my content for more winter-friendly outfit ideas!

Don’t forget to visit my LTK storefront to shop all my outfits in one central place.

Please feel free to leave a comment telling me how you are wearing skirts this winter season or visit The Fabulous After 40 Dressing Room, which you can join right here.

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