Winter is the perfect time to break out your collection of long skirts. Pairing these feminine garments with boots creates an effortlessly chic look. If you’re wondering how to pull off long skirts with boots stylishly, you’ve come to the right place.

Here’s a quick answer: Choose a long skirt that hits below the knee or at the ankle. Pair it with knee-high or over-the-knee boots in a coordinating color. Accessorize with tights, sweaters, jackets and scarves. Stick to neutral colors and textures for an elegant winter style.

Choose the Right Long Skirt Length

When it comes to styling winter long skirts with boots, the first step is to choose the right length for your skirt. The length of your skirt can greatly impact the overall look and feel of your outfit. Here are some tips to help you find the perfect length:

Mid-calf or ankle length

For a chic and sophisticated look, opt for a long skirt that falls either at mid-calf or at the ankle. This length is flattering on most body shapes and works well with different types of boots. Whether you prefer knee-high boots or ankle boots, a mid-calf or ankle-length skirt will create a balanced and elegant silhouette.

Avoid mini or midi lengths

While mini and midi skirts are great for warmer months, they may not be the best choice for winter styling with boots. Mini skirts can leave your legs exposed to the cold weather, while midi skirts can sometimes create an unflattering proportion when paired with boots.

It’s best to stick to longer lengths that provide more coverage and warmth during the winter season.

Consider A-line or maxi skirt shapes

When selecting a long skirt for winter, consider opting for A-line or maxi skirt shapes. A-line skirts are fitted at the waist and gradually flare out towards the hem, creating a flattering and feminine silhouette.

Maxi skirts, on the other hand, are long and flowy, adding a touch of elegance to your winter outfit. Both A-line and maxi skirts pair well with boots and can be styled in various ways to achieve a chic look.

Remember, the key is to choose a long skirt length that not only suits your body shape but also complements your choice of boots. Experiment with different lengths to find the one that makes you feel confident and stylish.

Pick Boots That Complement Your Skirt

Choosing the right boots to pair with your winter long skirts is essential for achieving a chic and stylish look. By selecting the right boots, you can enhance the overall outfit and create a fashionable ensemble. Here are some tips to help you pick the perfect boots that complement your skirt:

Over-the-knee boots

Over-the-knee boots are a fantastic choice for adding drama and sophistication to your winter long skirt outfits. These boots elongate the legs and create a sleek silhouette. Choose a pair in black or a neutral color to easily match with different skirt styles.

For a trendy look, try pairing a pleated long skirt with over-the-knee boots and a chunky sweater.

Knee-high boots

Knee-high boots are a versatile option that works well with various skirt lengths. These boots provide warmth and can be dressed up or down depending on the occasion. Pair knee-high boots with a midi skirt for a polished and elegant look.

Opt for a monochromatic outfit by choosing boots in a similar color to your skirt.

Ankle boots with taller shafts

Ankle boots with taller shafts are a great choice for winter long skirts as they provide coverage and add a touch of edge to your outfit. These boots look fantastic with maxi skirts or long flowy skirts. Add a cozy sweater and a statement belt to complete the look.

Remember to choose ankle boots that have a taller shaft to ensure they are visible under the skirt.

Match colors and textures

When styling your winter long skirt with boots, it’s important to consider color coordination and texture matching. Pairing boots in a similar color family as your skirt can create a cohesive and put-together look.

Additionally, experimenting with different textures can add visual interest to your outfit. For example, try pairing a suede skirt with leather boots for a contrasting yet stylish combination.

Remember, the key to creating a chic look with winter long skirts and boots is to have fun and experiment with different styles. Embrace your personal style and confidence, and you’ll rock any outfit combination!

Style Your Outfit for the Season

When it comes to styling winter long skirts with boots, there are several key elements to consider. By following these tips, you can create a chic look that is both fashionable and weather-appropriate.

Layer with sweaters, jackets, and coats

One of the best ways to style a winter long skirt with boots is to layer your outfit with cozy sweaters, jackets, or coats. This not only adds warmth but also creates a stylish and layered look. Opt for chunky knit sweaters or tailored jackets that complement the length and style of your skirt.

Experiment with different textures and colors to add depth and interest to your outfit.

Wear opaque or patterned tights

When wearing long skirts in the winter, it’s essential to keep your legs warm. Pair your skirt with opaque tights in a matching or complementary color to create a streamlined look. Alternatively, you can choose patterned tights to add a touch of fun and personality to your outfit.

Consider patterns like houndstooth, polka dots, or even subtle floral designs to elevate your look.

Incorporate scarves and hats

To complete your winter ensemble, don’t forget to incorporate scarves and hats into your outfit. These accessories not only keep you warm but also add a stylish touch. Opt for chunky knit scarves in neutral or bold colors that complement your skirt and boots.

Additionally, choose a hat that flatters your face shape and adds a touch of sophistication to your look. Whether it’s a cozy beanie or a wide-brimmed fedora, the right hat can elevate your outfit to the next level.

Stick to darker, neutral colors

When styling winter long skirts with boots, it’s generally best to stick to darker, neutral colors. Black, gray, navy, and burgundy are all great choices that can easily be paired with different boots and tops.

These colors not only give off a chic and sophisticated vibe, but they also tend to be more forgiving when it comes to hiding any potential winter stains or dirt that may accumulate during the colder months.

Accessorize for a Polished Look

When it comes to styling winter long skirts with boots, the right accessories can take your outfit to the next level. Not only do accessories add a touch of personality, but they also help to create a polished and chic look. Here are some accessory ideas to consider:

Leather bags

A leather bag is a classic accessory that adds sophistication to any outfit. Opt for a structured leather bag in a neutral color like black, brown, or tan. The sleek and timeless design of a leather bag complements the elegance of a winter long skirt and boots ensemble.

Plus, they provide ample space to carry your essentials while keeping your hands free.

Structured totes

For those who need more space for their belongings, a structured tote bag is a great option. These bags are not only practical but also add a touch of sophistication to your outfit. Look for a tote with clean lines and minimalistic design that complements the overall look of your winter skirt and boots.

Statement jewelry

To add a touch of glamour to your winter long skirt and boots outfit, consider incorporating statement jewelry. A bold necklace or a pair of oversized earrings can instantly elevate your look. Opt for pieces that have unique designs or feature eye-catching gemstones or metals.

These accessories will draw attention and make a statement.

Bold belts

Adding a belt to your winter long skirt and boots ensemble can help define your waist and create a more flattering silhouette. Opt for bold belts with interesting buckles or unique designs. A contrasting belt color can also add a pop of color to your outfit, especially if you’re wearing neutral-colored skirts and boots.

Remember, accessorizing is all about personal style, so feel free to experiment and find what works best for you. By adding the right accessories, you can elevate your winter long skirt and boots look to a whole new level of chicness.

Avoid Fashion Faux Pas

Don’t let your skirt drag on the ground

When styling winter long skirts with boots, it’s important to avoid the fashion faux pas of letting your skirt drag on the ground. Not only does it look sloppy, but it can also damage the hem of your skirt.

Make sure to choose a skirt length that is appropriate for your height and pair it with boots that have a heel or platform to give you some lift. This will help to prevent your skirt from grazing the ground and keep you looking chic and put together.

Skip mini and midi lengths

While mini and midi skirts can be fun and flirty during the warmer months, they may not be the best choice when it comes to styling winter long skirts with boots. These shorter lengths can leave too much skin exposed to the cold weather and may not provide enough coverage for a chic winter look.

Instead, opt for a longer length skirt that falls just below the knee or even to the ankle. This will not only keep you warm but also create a more sophisticated and elegant silhouette.

Don’t pair with pumps or strappy sandals

When it comes to footwear, avoid pairing your winter long skirts with pumps or strappy sandals. While these styles may work well with shorter skirts during the warmer months, they can look out of place and impractical when worn with longer skirts and boots.

Instead, opt for ankle boots or knee-high boots that complement the length of your skirt. These styles will not only keep your feet warm but also add a touch of edge and sophistication to your overall look.

Don’t overload on accessories

When styling winter long skirts with boots, it’s important to strike the right balance with your accessories. Avoid overloading on accessories that can overwhelm your outfit and take away from the chicness of the look. Instead, choose one or two statement pieces that complement your skirt and boots.

For example, a chunky knit scarf or a statement belt can add a touch of personality to your outfit without overpowering it. Remember, less is often more when it comes to accessorizing.


Long skirts and boots make the perfect winter duo. Follow these tips on skirt length, boot height, layering essentials, chic accessories and common mistakes to avoid. With the right styling, you’ll look poised, elegant and cozy all season long in your winter long skirt and boots.

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