10 Best Shoes To Wear with Leggings (2021 Style Guide)

When it comes to comfortable and versatile pants, leggings have taken over the fashion world, becoming a must-have for casual and smart casual outfits. In the past, leggings were only worn as gym or yoga pants, but this functional wardrobe staple has transitioned into an everyday item that can be dressed up or down to suit a variety of styles. While leggings are often considered athleisure pieces, you can style these bottoms to fit any occasion. In the process, you’ll need to think about your footwear to create the right look. What shoes you wear with your leggings will set the tone of your outfit. Some women will choose sneakers, loafers and sandals for a casual look, while others may prefer heels and boots for a trendy aesthetic. Whether you need footwear that will elevate your jeggings or cute shoes to match your leggings outfit in the winter, summer, spring or fall, there are many easy and fashionable ideas to consider! To help you look stylish and cute, we’ve compiled a list of the best shoes to wear with leggings. From ankle boots to flats to tennis shoes, explore these different types of footwear to find shoes that go with leggings.

Shoes To Wear with Leggings

Shoes To Wear with Leggings


Sneakers perfectly fit the athleisure aesthetic you’re probably aiming to achieve with leggings. You can dress your leggings with leather sneakers, tennis shoes, trainers, or even high-tops. For a supreme sporty look, combine your lace-up sneakers with matching pieces from Adidas, Nike, Reebok, and other popular athletic brands. If you want a pop of color or a pattern, you’ll want to try styling your footwear with a pair of leggings from brands like Lululemon, Alo Yoga, or The Upside. Adding a crop top or jersey with your high-top sneakers and leggings will provide the ultimate casual-cool look. Versatile and fashionable, leggings can work with a dress or be teamed up with an oversized shirt, knit sweater, turtleneck and/or jacket. Top your outfit off by styling your hair with a baseball cap or high ponytail. If you’re working out, it’s best to keep your accessories at a minimum so they don’t get in the way, but feel free to add a practical crossbody bag or backpack for your valuables.

Leggings with Sneakers

Slip-On Sneakers

While they don’t scream “athlete”, slip-on sneakers still add a sporty edge to your ensemble. You’ll want to pair your solid-colored buttery soft leggings and easy slip-on sneakers with equally smooth pieces, like an oversized sweater or sweatshirt, or a loose tank top. Depending on the weather, you may want to add a roomy coat, like a puffy jacket or trench. As for accessories, feel free to add minimal jewelry that won’t slip off easily, like small studded earrings, stacked rings, or a wrap bracelet.

Slip-On Shoes with Leggings


Going up the casual chain, loafers are another easy slip-on option to pair with your leggings. You may decide to choose a less athletic fabric for your leggings, like leather or velvet, which you can easily match with leather or velvet loafers. Upgrade the look of your loafers and leggings by wearing an elegant button-down blouse or a ribbed turtleneck with a blazer to top it off. When combining loafers and leggings, you can incorporate accessories that make more of a statement, like hoop earrings, a chunky necklace, and bangles for jewelry, as well as a large carry-all tote.

Loafers with Leggings

Over-The-Knee Boots

Leggings are the easiest type of pants to slip into over-the-knee boots, and the combination will ensure you remain warm, comfortable, and stylish. While most women will put on skinny jeans, over-the-knee boots are versatile, and look sexy and sleek with leggings. Whether you choose a flat riding boot or a tight stiletto, this boot style can be paired with casual and semi-formal outfits for a stunning finish.

Regardless of what type you wear, over-the-knee boots certainly make a statement, and how much of one you want to make will depend on your color and pattern choice. Black and brown over-the-knee boots are classic and will never go out of style. For a bolder look, try a louder color like bright red or a trendy pattern like snakeskin. To complete the look, wear your leggings and long boots with a fitted long-sleeved top and a leather jacket. You can also style the pair with an oversized knit sweater, a long shirt dress, or a cute maxi dress.

Leggings with Boots


Heels are a great way to transition your leggings from daytime to night. You don’t just have to have on a silky blouse to make your outfit stand out. Don’t be afraid to wear your leggings with a form-fitting dress or skintight skirt that hugs your curves. And if it’s a little chilly, consider wearing a stylish cape or poncho. Finally, grab your favorite glittery or glossy clutch for a sophisticated finish.

Leggings with Heels

Ankle Boots

As classic footwear that every woman owns, ankle boots offer versatility and style that can be matched with leggings. While booties may not be as edgy as over-the-knee boots, you can’t go wrong pairing ankle boots with leggings for a chic and timeless look. You can also decide on the type of heel, choosing to wear heeled ankle boots for a fashionable look or flat booties for a relaxed vibe. Ankle boots also come in multiple colors such as black, brown and tan as well as a range of styles, from combat to Chelsea boots, giving you even more selection.

Flat heel ankle boots are great for casual outfits created by styling leggings with a simple t-shirt or oversized blouse layered with a button-down shirt. Wearing a wedged or stacked heel with suede will upgrade your look to smart casual, designing the perfect ensemble for work. If you’re looking for something truly elegant, choose leather ankle boots with a pointed toe and heel. Add a warm turtleneck or cashmere sweater to complete the look.

Ankle Boots with Leggings


Flats pair perfectly with simple, solid-colored leggings. If you don’t want your outfit to be too understated, try throwing on a blazer in a bright hue, like electric blue or hot pink, and mix in some chunky accessories. For a full-on ballerina look, add a comfortable bodysuit to tuck into your leggings and tie your hair in a bun. Or throw on an oversized sweatshirt with an exposed shoulder if it’s not too cold outside.

Flats with Leggings


Sandals and leggings go great together no matter the heel height. If you want a modern and comfortable ensemble, dress a pair of slip-on or strappy flat sandals with your outfit. For a summer look that will keep you cool and fresh, wear espadrilles that wrap around the ankle. For an edgy evening look you can wear out, leggings with strappy sandals are fashionable and stunning. Just make sure that if you’re going to the club, choose footwear that will stay on while you dance the night away. Since sandals are easy to style with leggings, you can couple them with practically anything. From a crop top to a basic blouse to a graphic tee, leggings and sandals are a natural fit. Just add a crossbody bag and you’re all set to go!

Leggings with Sandals

Knee High Boots

Knee-high boots with leggings are the epitome of cold-weather cool. While leather and suede knee-high boots are the most common, feel free to experiment with other materials like fur or shearling for ultimate comfort. Throw on a sweater in the size and fabric of your choice, and top off your look with a knitted infinity scarf and warm beret.

Leggings and Knee High Boots


Slides are easy slip-on sandals that toe the line between fitness and fashion, making them ideal for athleisure attire. Play up your slides and leggings by wearing a graphic tee with a fun design and a leather jacket or a chunky cardigan in the colder months. Pair them with a bucket bag or medium-sized handbag in a solid color, and wear simple jewelry in silver, gold, or rose gold.

Slides with Leggings

What Shoes To Wear with Leggings

  • Sneakers, slip-ons, and slides provide more of a sporty, athletic look, and you’ll want to accessorize them minimally, especially when working out. Keep your look simple with a crop top, graphic tee, or jersey.
  • Loafers, sandals, and ballet flats paired with leggings offer an effortlessly smart casual look, and are great for lounging around the house, running errands, or grabbing coffee with a friend. Pair them with a button-down blouse or knit sweater.
  • Ankle boots and knee-high boots are another smart casual outfit idea and can be practical to wear with leggings during the fall and winter. Top off your look with an equally warm cardigan or coat.
  • When it comes to sexy attire, you’ll want to dress your leggings with classy over-the-knee boots or heels, especially for a first date or girl’s night out. Style this outfit with a silky blouse in the spring and summer, or a cashmere sweater during the cooler months.

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