We Found The 20 Best Shoes to Wear With Leggings

Woman wearing leggings

Getty Images / Edward Berthelot 

Oh, leggings, our most faithful fashion companion. Whether you're tossing them on for a quick grocery run, workout, or date night, the stretchy bottoms work for many occasions. While there is plenty of debate on the "are leggings pants" questions (they are), no one can doubt their versatility. 

However, while there are so many ways to wear leggings, most of us get stuck on what shoes to wear with them. Are straps okay? Is pairing heels with leggings tacky? Well, you can finally put your questions to rest. Ahead, we compiled 20 different pairs of shoes that go with most of your legging collection.

01 of 20

Lace-Up Sneakers

The Lace Up
Rothy's The Lace Up $165.00

The pairing of sneakers and leggings is an iconic duo. These lace-up sneakers from Rothy’s take the trendy white sneaker look and give it a retro twist with the added yellow and orange stripes. Pair with your favorite leggings, and you’re ready to go. Plus, these sneakers are made of recycled plastic water bottles, so it’s both cute and eco-friendly. 

02 of 20


The Starling
Birdies The Starling $95.00

For a look that blends comfort and chic, pair leggings with some velvet loafers. Add an oversized blazer and a crisp white button-down, and you have a put-together look that is business casual and very comfy. Plus, these black loafers are Meghan Markle-approved. 

03 of 20

Knee High Boots

Maryana Boot
Schutz Maryana Boot $238.00

If you’re looking to dress up your favorite pair of black leggings, add a statement knee-high boot like this wild pair from Schutz. Its snakeskin print and high heels make any look feel effortlessly cool. Pair with your favorite black leggings and a little dress, and you’re ready to go out. 

04 of 20


Freebirds Mabel $195.00

These oxfords from Freebird blend the classic Oxford style with some western flair. Pair these with your favorite black leggings and an oversize white button-down or a chunky knit cardigan for some fall vibes year-round. 

05 of 20


Vala Black Patent + Bworldly Black Patent
Steve Madden Vala Black Patent + Bworldly Black Patent $155.00

There’s always a little controversy between leggings and heels. Do you wear them together, or do they look tacky? Bottom line: it’s all about how you style it. A pair of black pumps would go great with a pair of leather leggings and a dressy cami. Add a leather jacket for an extra edge. 

06 of 20

Combat Boots

Dune London Pagola $265.00

The '90s are back, with our favorite grunge shoe coming back into style. Pull out your trusty Doc Martin, or elevate your look with these biker boots from Dune London. Pair with some black leggings, a graphic tee, and a flannel, and you’re ready to go.

07 of 20

Slip-On Sneakers

Ranger Slip On Sneaker
Naturalizer Ranger Slip On Sneaker $89.00

If you love the sneaker and leggings look but cannot deal with laces, slip-on sneakers make the sporty look you’re going for more relaxed and casual. Throw on your favorite slip-ons and your activewear leggings for a weekend workout, or slip on these sneakers from Naturalizer and some chic leggings for a dresser but still casual look. 

08 of 20

Ankle Boots

SB-Cady Rhinestones
Betsey Johnson SB-Cady Rhinestones $149.00

Ankle boots are a fall fashion staple that goes with just about anything in your closet, including your favorite leggings. While you can pair any ankle boot when any pair of leggings, I’m personally obsessed with these rhinestone booties from Betsey Johnson. Pair these with some black leggings, a black top, and a rhinestone mask to create a rocking mirrorball look. 

09 of 20


Classic College Slipper
Stubbs & Wootton Classic College Slipper $500.00

While more people are getting vaccinated and more places start re-opening, many people still want to keep their comfy clothes as they transition from quarantine to post-vaccine life. That is why the slipper and leggings look is perfect for this phase. Pair these clever velvet slippers with a fun legging print, and you’re ready to go outside.

10 of 20

Ballet Flats

The Skim
Rebecca Allen The Skim $75.00

Ballet flats are an easy, ready-to-go option that you can wear in almost all seasons (depending on where you live) and can be dressed up or down, depending on the occasion. Adding a flat with a print or pop of color like these lets your outfit stand out. 

11 of 20

Rain Boots

Women's Original Tall Rain Boots
Hunter Women's Original Tall Rain Boots $150.00

Leggings are perfect for a rainy day because of how easy they are to tuck into high rain boots. Toss on your tall rain boots, your leggings, and your favorite raincoat, and you’re ready to go.

12 of 20

Kitten Heels

Jojo Braided Heels
Free People Jojo Braided Heels $140.00

Kitten heels work great with leggings as they give the right height you need to balance out your leggings without looking off-balanced. The trick is to wear capri-length legging with your kitten heel shoe (or any shoe with a strap) to highlight the shoe while showing a bit of skin.

13 of 20

Flat Espadrilles

Ocean Stroll Espadrilles
Kate Spade Ocean Stroll Espadrilles $98.00

Flat espadrilles are another favorite in the "slip on and go" category. They're great if you are tired of flats and sneakers, but it’s too warm for boots. Espadrilles can instantly make any outfit chic, even your favorite leggings you’ve worn for years. Pop them on with a cute boat neck shirt and some leggings, and you're ready for the day. 

14 of 20

Ankle Strap Shoes

Kels Retro Sandals
Chelsea Paris Kels Retro Sandals $595.00

As with the kitten heels, you want to wear capri-length leggings with any shoe that has an ankle strap. Opt for a shoe with a single ankle strap only, as any additional straps or length could make the look feel clunky. Ankle strap shoes and leggings can be dressed up or down, depending on your mood, but they're always perfect for a nice sunny day. 

15 of 20

Over-The-Knee Boots

Tayla Faux Suede Heeled Boot
Vici Collection Tayla Faux Suede Heeled Boot $54.00

Again, leggings are made for very high boots as they are easy to slip on and off. Plus, over-the-knee boots make your simple legging and sweater outfit stand out with little effort. 

16 of 20


Tuesday Mule
Brother Vellies Tuesday Mule $495.00

Trendy, effortless, and easy to slip on as you head out the door, mules are an interesting shoe that allows you to play with your style and outfit choices. These zebra print mules from Brother Vellies add a splash of edginess to your leggings look.

17 of 20


Ilamoye Slide Mule
SheKudo Ilamoye Slide Mule $210.00

A favorite summer go-to, slides are great to pair with leggings because there are so many ways to style the specific combination. From sporty to streetwear, slides work with almost any look you're going for.

18 of 20


Color Chuck Taylor All Star
Converse Color Chuck Taylor All Star $60.00

Almost all sneakers go great with leggings, but there’s something special about a high-top sneaker like these brightly colored Converse. Probably because there are so many ways to style it, you can go sporty with a pair of leggings and a muscle tank, or you can unleash your inner hipster with leggings and an oversize flannel. You can even elevate the usually casual kicks with a little dress. 

19 of 20

Square Toe Shoes

Croc Embossed Leather Ballerina Flats
& Other Stories Croc Embossed Leather Ballerina Flats $99.00

To balance out the effects of the tight fit of your leggings, square-toe shoes like these deliver a contrasting effect that creates a more proportional and finished look. Plus, you can style them in multiple ways, so you'll always look on point. 

20 of 20

Hiking Boots

K-6 Boot
Eddie Bauer K-6 Boot $150.00

With warmer weather on the horizon, it’s an ideal time to enjoy nature with a hiking adventure. Grab a solid pair of athletic leggings and your favorite hiking boots and get lost in nature. Or, if you aren’t much of an "outdoorsy" type, hiking boots and legging are still a cute outside pairing for a rustic, cozy vibe. 

Related Stories