Winter skirts and boots are a chic staple during the colder months. If you’re wondering how to pair these items for a stylish and cozy outfit, you’ve come to the right place.

Here’s a quick overview of how to dress up your winter skirt with the perfect boots: go for knee-high boots in leather or suede paired with a midi or maxi skirt. Tights add warmth and you can finish the look with a stylish coat.

Details like plaid prints, fuzzy sweaters, and slouchy boots make it extra trendy.

In this comprehensive guide, we’ll cover everything you need to know about achieving the perfect winter skirt and boots outfit. Read on for tips on choosing the right skirt style, boot height and material, layering pieces, and accessorizing for a polished cold-weather ensemble.

Pick the Right Skirt Silhouette and Length

When it comes to styling winter skirts with boots, choosing the right silhouette and length is key to achieving a chic cold-weather outfit. Different skirt styles can create different looks and flatter different body types. Here are some popular skirt silhouettes and lengths to consider:

Midi and Maxi Skirts

Midi and maxi skirts are great options for winter as they provide extra coverage and warmth. Midi skirts typically fall below the knee and above the ankle, while maxi skirts are longer and reach the ankles or floor. These longer lengths are perfect for pairing with knee-high or over-the-knee boots.

Not only do they keep you warm, but they also create a stylish and sophisticated look.

A-Line or Pleated Skirts

A-line and pleated skirts are versatile options that can be dressed up or down for various occasions. A-line skirts are fitted at the waist and gradually flare out towards the hem, creating a flattering silhouette for all body types.

Pleated skirts have folds or pleats that add texture and movement to the outfit. Both A-line and pleated skirts can be paired with ankle boots or knee-high boots, depending on the length and style of the skirt.

Patterned Skirts

Adding patterns to your winter skirt can bring a touch of fun and personality to your outfit. Whether it’s plaid, floral, or geometric prints, patterned skirts can make a statement while also keeping you warm. Pair them with solid-colored boots to let the skirt be the focal point of your look.

Experiment with different patterns and colors to create a unique and eye-catching ensemble.

Remember, the key to styling winter skirts and boots is to find the right balance between fashion and functionality. Choose skirts that suit your body type and pair them with boots that complement the length and style of the skirt.

By selecting the right skirt silhouette and length, you can effortlessly create a chic and stylish cold-weather outfit.

Choose Complementary Boots

When it comes to styling winter skirts, choosing the right boots can make all the difference. The perfect pair of boots can elevate your outfit and keep you warm and stylish throughout the cold weather. Here are some tips on choosing complementary boots for your winter skirts:

Over-the-Knee Boots

Over-the-knee boots are a popular choice for winter outfits. They add a touch of sophistication and can instantly make any skirt look chic. These boots are perfect for shorter skirts or mini skirts, as they provide extra coverage and warmth.

Pair them with a chunky knit sweater and a mini skirt for a cozy and trendy look. For a more polished ensemble, try pairing them with a tailored pencil skirt and a blazer.

Knee-High Boots

Knee-high boots are versatile and can be paired with various skirt lengths. They provide more coverage than over-the-knee boots, making them ideal for colder temperatures. For a casual and effortless look, pair knee-high boots with a midi skirt and a cozy sweater.

This combination is perfect for a day out or a casual brunch with friends. If you’re looking for a more dressed-up outfit, pair knee-high boots with a maxi skirt or a pleated skirt for a feminine and elegant look.

Ankle Boots

Ankle boots are a staple in any winter wardrobe. They are versatile and can be paired with almost any skirt length or style. For a casual and laid-back look, pair ankle boots with a denim skirt and a chunky sweater. This combination is perfect for running errands or a weekend outing.

If you want to dress up your outfit, pair ankle boots with a leather skirt and a blouse. This combination exudes confidence and style.

Remember to choose boots that complement your personal style and the occasion you’re dressing for. Experiment with different styles and lengths to find the perfect pair of boots that make your winter skirt outfit truly chic and fashionable.

Don’t Forget Layers

When it comes to styling winter skirts and boots, layering is key. Not only does it add warmth, but it also adds depth and dimension to your outfit. Here are a few layering options to consider:

Opaque Tights

One of the easiest ways to add warmth to your winter skirt and boot ensemble is by wearing opaque tights. Not only do they provide an extra layer of insulation, but they also add a touch of elegance to your outfit. Opt for black or dark-colored tights to create a sleek and sophisticated look.

If you want to experiment with patterns, try houndstooth or plaid for a stylish twist. Remember to choose tights with a high denier count for maximum warmth.

Fuzzy Sweaters and Cardigans

Pairing your winter skirt with a fuzzy sweater or cardigan is a great way to stay cozy and fashionable. Look for sweaters made from soft and warm materials like cashmere or wool. A chunky knit cardigan can also add a touch of coziness to your outfit.

Experiment with different textures and colors to create a chic and winter-appropriate look. Don’t be afraid to mix and match patterns, like pairing a plaid skirt with a striped sweater for a bold and stylish combination.


Don’t underestimate the power of socks when it comes to keeping your feet warm during the winter months. Opt for knee-high or over-the-knee socks to create a layered look that adds both warmth and style. Choose socks in a contrasting color to your skirt and boots to make a statement.

For added comfort, look for socks with a bit of stretch and cushioning. Embellished socks with lace or ruffles can also add a feminine touch to your outfit.

Remember, winter dressing is all about finding the perfect balance between style and functionality. By layering with opaque tights, fuzzy sweaters and cardigans, and adding socks, you can create a chic and cozy cold-weather outfit that will keep you looking fabulous all season long.

Accessorize for a Complete Look

When it comes to styling winter skirts and boots, accessorizing is key to achieving a chic cold-weather outfit. Adding the right accessories can elevate your look and make a statement. Here are some ideas on how to accessorize for a complete winter outfit:

Coats and Jackets

One of the most important accessories for a winter outfit is a coat or jacket. Not only does it keep you warm, but it also adds style to your overall look. Consider opting for a long wool coat or a trendy puffer jacket.

These options not only provide warmth but also give a fashionable touch to your outfit. Don’t be afraid to experiment with different colors and patterns to make a bold statement.


Scarves are another great accessory to add to your winter skirt and boots ensemble. They not only keep your neck warm but also provide an opportunity to add a pop of color or texture to your outfit. A chunky knit scarf in a vibrant hue can instantly liven up a neutral-toned outfit.

Alternatively, a patterned scarf can add visual interest and create a focal point.

Hats and Beanies

No winter outfit is complete without a stylish hat or beanie. Not only do they keep your head warm, but they also add a touch of personality to your look. A wide-brimmed fedora can give your outfit a sophisticated edge, while a cozy beanie can add a playful and casual vibe.

Choose a hat or beanie that complements your outfit and fits your personal style.

Remember, when accessorizing, it’s important to strike a balance. Don’t overwhelm your outfit with too many accessories, but also don’t be afraid to experiment and have fun with your winter look. By adding the right coats and jackets, scarves, hats, and beanies, you can create a chic and stylish cold-weather outfit that will turn heads wherever you go.

Putting It All Together: Sample Outfits

Plaid Midi Skirt with Knee-High Boots and Cardigan

For a chic and cozy winter outfit, pair a plaid midi skirt with knee-high boots and a cardigan. The plaid print adds a touch of sophistication and the midi length keeps you warm while still looking stylish. Pair it with knee-high boots to add a bit of edge and keep your legs warm.

Complete the look with a cozy cardigan for added warmth and comfort. This outfit is perfect for a day at the office or a casual weekend brunch with friends.

Maxi Skirt with Over-the-Knee Boots and Fuzzy Sweater

For a more dramatic winter look, try pairing a maxi skirt with over-the-knee boots and a fuzzy sweater. The maxi skirt adds a touch of elegance and the over-the-knee boots make a statement. Pair it with a fuzzy sweater to add texture and warmth.

This outfit is perfect for a night out or a special occasion. You’ll be sure to turn heads with this stylish ensemble.

Leather A-Line Skirt with Ankle Boots and Poncho

For a trendy and edgy winter outfit, opt for a leather A-line skirt paired with ankle boots and a poncho. The leather skirt adds a touch of sophistication and the A-line silhouette flatters all body types. Pair it with ankle boots for a chic and comfortable look.

Complete the outfit with a cozy poncho to keep you warm and stylish. This outfit is perfect for a day of shopping or a night out with friends.

Remember, the key to styling winter skirts and boots is to balance warmth and style. Layering is key, so don’t be afraid to add tights, leggings, or thermal socks for that extra warmth. Additionally, don’t forget to accessorize with scarves, hats, and gloves to complete your cold-weather look.

Have fun experimenting with different combinations and find the style that suits you best!


Winter skirts and boots make such a chic pairing for the colder months. By selecting the right skirt length, boot height, and cozy layers, you can create an outfit that’s both fashionable and functional.

Focus on textures like leather, suede, and fuzzy knits to add visual interest. Have fun pairing different prints and patterns together too. Top it off with warm accessories like scarves, hats, and coats tied around your waist or shoulders.

With all these tips in mind, you can step out in style all winter long. Stay cozy and cute in your winter skirt and boots outfit!

Similar Posts