We all know that leggings are for more than just hitting the gym—from the yoga mat to the cubicle, these classic bottoms have become a comfortable and stylish winter wardrobe staple. But as temperatures begin to drop, it’s important to choose the right footwear to pair with your favorite leggings, ensuring you stay warm and look great, regardless of the weather.

The right shoes not only enhance your overall look but also provide the support and comfort you need to stay cozy during the colder months. Whether you’re running errands, heading to the office, or enjoying a casual outing with friends, the right winter footwear can take your legging game to the next level.

With a variety of styles available—from chic ankle boots to cozy slip-on sneakers—there’s no shortage of options to match your personal aesthetic. In this article, we’ll explore the best shoes to wear with leggings in winter so that you can look fabulous and feel confident no matter the occasion.

 

Boots That Work Best with Leggings

As winter approaches, the quest for the perfect women’s boots to pair with black leggings becomes essential. The right boots not only help keep your feet warm in winter but also highlight your unique style. 

Here’s a look at some of the best boot options to complement your favorite leggings this season:

 

Ankle Booties

Ankle boots are the perfect choice for effortlessly transitioning between fall and winter. If you don’t know how to wear ankle boots fashionably, consider combining them with a fun pair of leather leggings or a sweater dress. Whether you’re drawn to heeled and wedge boots for a dressier vibe or prefer flat styles for everyday wear, ankle boots provide an easy way to elevate your ensemble during the winter months.

For the perfect women’s winter outfit idea, try pairing your ankle boots with thicker, textured leggings and an oversized knit sweater. It’s all about comfort and warmth! If you’re aiming for something a bit more sophisticated, heeled ankle boots are your best friend. A sleek stiletto or a block heel—like the one seen in Vionic’s Barstow Heeled Ankle Boot—can instantly dress up a pair of regular leggings, giving you that polished look while still showcasing your personal style.

For an elevated ‘fit, opt for high-waisted leather leggings in a solid color, then layer with a tailored blazer or a structured tunic. Then, pair the look with an elegant wedge, like Vionic’s Aria Wedge Ankle Boot. This combination is perfect for a day at the office and easily transitions to happy hour with friends, ensuring you look sleek no matter where you’re headed. 

 

Combat Boots

For a bit of an edge, combat boots are an excellent choice, bringing a blend of rugged charm and practicality to any casual outfit. Their sturdy design also offers durability, making them ideal for navigating cold, wet, or snowy conditions. 

The added height and structure of combat boots create a balanced silhouette when paired with the sleekness of leggings, giving a stylish edge to a casual look. Whether you choose classic black for a timeless ensemble or experiment with bold colors, combat boots can easily complement both neutral and patterned leggings. 

Their lace-up design not only adds a trendy vibe but also allows for a customizable fit, ensuring comfort throughout the day. When it comes to styling combat boots, they can effortlessly transition from day to night. Pair them with oversized sweaters or fitted jackets for a cozy daytime outfit, then switch to a stylish top for an evening out.

 

Chelsea Boots

Chelsea boots are another fantastic option that effortlessly blends style with functionality. With their convenient slip-on design, they’re perfect for everyday wear, allowing you to get ready quickly without sacrificing flair. 

Don’t know how to wear Chelsea boots? The sleek silhouette of Chelsea boots pairs beautifully with leggings, making them a go-to option for various occasions. Whether you’re heading to your 9 to 5, running to the grocery store, or preparing for date night, these boots transform any outfit during the winter months.

They work especially well with fitted or high-waisted leggings. They are even classic shoes to wear with dresses in winter for a cozy and put-together look. Plus, the versatility of Chelsea boots means you can dress them up with a stylish blouse or keep it casual with a cozy sweater. 

 

Knee-High Boots

For those colder days, knee-high boots are a practical and fashionable option. They not only provide extra warmth but also create a streamlined silhouette when paired with leggings. 

So, how do you wear knee-high boots in winter weather? Choose tall boots made from materials like leather or faux leather to add a bit of edge. A heeled version can elevate your outfit for a night out, while options with a flatter sole, like Vionic’s Fallbrook Knee High Boot, keep things comfortable for daytime adventures. 

For a blend of comfort and elegance, choose Vionic’s Ashland Tall Wedge Boot. It adds a few extra inches of height while providing the support and stability you need.

 

Top Shoe Styles to Pair with Leggings

Boots are a must-have for the winter months, but they’re far from your only footwear option this season. Curious about how women’s sneakers, loafers, and slip-ons pair with leggings? Here are a few of our top recommendations for shoes that can elevate your leggings while still ensuring cold-weather comfort and year-round support. 

 

Chunky Sneakers

Chunky sneakers have made a major comeback and are perfect for creating a laid-back, trendy look with leggings. Plus, their cushioned soles provide comfort for long days, making them ideal for running errands or meeting up with friends.

Look for fun textures (like mesh and leather) or unique patterns to add a pop of personality to your winter wardrobe. And even more good news? This style works well with both basic and printed leggings.

 

Slip On Loafers

For a more polished appearance, slip-on women’s loafers are an excellent choice. This classic shoe provides the perfect blend of sophistication and comfort. Bonus points for finding a pair with arch support and cushioned insoles like Vionic’s Uptown Loafer. 

These shoes can easily elevate your leggings, making them suitable for work or a casual lunch date. Choose neutral tones for versatility or metallic finishes for a chic twist.

 

Mules and Slip-Ons

If you’re looking for easy-to-wear options, mules and slip-on shoes are a must. These styles provide comfort and convenience, making them perfect for days when you need to dress quickly but still want to look put together. 

Opt for styles with thick soles and warm materials, like wool or lined leather, to keep your feet cozy during colder months. Pair them with long leggings for a Parisian-inspired, effortless look.

 

Sneakers and Leggings: A Casual Pairing

When it comes to winter fashion, the combination of sneakers and leggings offers the ultimate in ease and flair. This pairing is not only practical but also effortlessly chic. Black leggings provide the flexibility needed for layering, while sneakers complete the outfit with a relaxed vibe.

To keep your look fresh, consider experimenting with different materials. Leather or faux leather sneakers offer a sleek, polished appearance that can elevate any casual outfit, while canvas options lend a more laid-back feel. Either way, both materials work beautifully with leggings, lending versatility to your winter wardrobe.

 

Tips for Accessorizing Your Leggings Outfit

Finding the right accessories, like the perfect pair of shoes, is an essential part of styling leggings in winter. With the right touches, you can transform a simple outfit into something that’s truly you. 

Check out these helpful tips for accessorizing your leggings ensembles for the colder months:

 

Combat Boots: Edgy Accessories

If you’re pairing your leggings with combat boots, select accessories that complement their bold vibe. For instance, consider layering a distressed denim jacket or a leather bomber for an effortlessly cool look. You can also opt for pieces like: 

 

• Chunky silver jewelry, statement rings, or layered necklaces
• A studded belt, which can enhance the rebellious feel of the outfit 
• A slouchy beanie to finish off the look 

 

Ankle Boots: Chic and Sophisticated

Ankle boots offer versatility that allows for a range of accessories. For a polished appearance, pair your leggings and booties with a tailored blazer or a long cardigan. Opt for elegant scarves in rich fabrics like cashmere or wool to add warmth and texture. 

Consider delicate jewelry, such as thin bracelets or minimalist earrings. A structured handbag can complete the look, making it perfect for both work and casual outings with friends.

 

Sneakers: Sporty and Fun

If you’re rocking sneakers with your leggings, embrace a sporty aesthetic with your accessories. Choose a graphic tee or a cozy hoodie to keep things casual. A vibrant backpack or crossbody bag adds functionality and flair. 

Colorful socks that peek out from your sneakers can bring an element of fun to your outfit. Don’t forget a stylish baseball cap or a colorful beanie to top off the look, perfect for those on-the-go days.

 

Knee-High Boots: Warm Layers

Knee-high boots are a great option if you’re trying to dress warm in cold weather. Pair them with oversized sweaters or chunky knit scarves to create a snug vibe. 

Opt for accessories like knit gloves or a soft beanie to keep warm while looking put together. A textured handbag can also add depth to your outfit and tie the whole look together.

 

Discover Vionic’s Versatile Footwear for Leggings

From chic ankle boots to trendy sneakers and cozy slip-ons, Vionic has the collection of footwear you need this winter—and beyond. Plus, thanks to our Vio-Motion Support technology, our footwear offers essential arch support and heel stability to keep you comfortable all season long.

When you shop Vionic, you invest in footwear that supports your lifestyle and prioritizes your comfort. Explore our collection to find the perfect pairs to seamlessly integrate with your leggings and make every outfit both fashionable and functional. 

 

Sources: 

InStyle. 12 Ways to Wear Boots With Leggings. https://www.instyle.com/boots-with-leggings-8421172 

InStyle. 22 Winter Leggings Outfits to Wear When It’s Freezing.  https://www.instyle.com/winter-leggings-outfits-7969013