6 Types of Shoes To Wear With Leggings

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Leggings are the unofficial uniform of doing it all, taking you from early flights to late lunches, from gym sessions to grocery runs. 

But while their ability to deliver on comfort makes leggings a smart addition to any capsule wardrobe, it’s the shoes you pair them with that take your outfit from “reading in bed” to “ready for anything.” 

Whether you’re all about cozy vibes or bold style, this guide walks you through the six best shoes to wear with leggings (plus some styles you should kick to the curb). 

What shoes go with leggings?

Whether you’re dressing up or keeping things casual, the perfect pair of shoes will help you win the leggings game. We’ve compiled the top shoe styles for leggings into a list of options that check every box, from comfort and versatility to outfit-elevating power. 

1. Ankle boots 

Ankle boots and leggings are the power couple of transitional fashion. The boots’ cropped height highlights the sleek silhouette of leggings, adding just the right amount of structure, whether you’re dressing up or down. 

Try pairing black leggings with ankle boots, a tucked-in mock-neck sweater, and an oversized plaid jacket. Gold hoops and a crossbody bag turn this casual look into a leggings outfit that’s put-together without trying too hard. In colder months, swap in warm Chelsea boots for extra comfort. 

‍Pro tip: Pair darker ankle boots with dark-color leggings to visually elongate your legs. 

‍What to look for: Boots that hit right around the ankle bone will complement the slim fit of the leggings without cutting off your leg line. Avoid wearing bulky boots with leggings since the extra mass will interrupt the clean silhouette. 

2. Sneakers 

‍Sneakers go with everything, and adding this staple to a leggings outfit adds instant cool-girl energy. They’re the sweet spot between comfort and fashion—perfect for road trips, errands, or wherever the day takes you.

Style sneakers and colorful leggings from a brand like Athleta with a cropped pullover and an oversized denim jacket. For that airport-to-street-style vibe, finish the look with sleek white sneakers, a baseball cap, and a mini backpack. 

‍Pro tip: Low-top sneakers keep the silhouette clean and streamlined; save bulkier athletic sneakers for full-on athleisure moments. 

‍What to look for: Go for classic sneaker styles like lace-ups or slip-ons in neutral tones. Want bonus points? Sneakers with a subtle platform sole add just enough lift without overwhelming the look. 

3. Heels

‍Heels dress up any outfit, and leggings are no exception. Whether you’re heading to dinner or a dressier event, the added height elongates your legs and adds polish to the leggings’ sleek silhouette. 

Pair leather leggings with heels, a satin blouse, and a long, tailored blazer. Finish with a clutch and a bold lip for a confident, out-for-the-night ensemble. 

‍Pro tip: Block or kitten heels will give you height without the wobble—perfect for looking put-together while staying steady on your feet. 

‍What to look for: Skip ankle straps, which break up the visual line of your leg. Instead, go for minimal styles in patent, leather, or suede. 

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4. Knee-high boots 

‍Knee-high boots are some of the best shoes to wear with leggings in winter. This combination creates a sleek, tucked-in look that’s both stylish and warm on chilly days. 

Try black leggings with knee-high boots, a chunky sweater dress, and a belted wool coat. Add a structured leather purse and statement earrings for an outfit that transitions smoothly from desk to dinner. 

‍Pro tip: Choose boots and leggings in similar tones for a sleek, work-ready vibe. 

‍What to look for: Go for boots with a slim shaft and a slight heel. A leather or faux-leather finish adds polish. 

5. Ballet flats 

‍Ballet flats are one of the best types of flats to wear with leggings. They add a feminine contrast and work perfectly for warm weather or low-key polished looks—more refined than athletic sneakers but less formal than heels. 

Try black leggings with blush-toned ballet flats, a striped bateau-neck top, and a cropped trench coat for a daytime outfit with a French-girl flair. Add a mini satchel and dainty gold jewelry to finish the look. 

‍Pro tip: Skip overly embellished styles; choose ballet flats with a simple bow or buckle to keep things chic. 

‍What to look for: Look for leather or patent flats with almond or square toes. Avoid pairs that are overly soft or worn out since they won’t hold their shape.

6. Loafers 

Loafers lend a preppy look to leggings’ slim profile—perfect for casual office days or elevated daytime outfits. They’re an easy way to embrace intentional fashion without looking like you tried too hard. 

Wear structured loafers with leather leggings, an oversized button-down, and a cropped sweater layered on top. For a crisp fall outfit, add a shoulder bag and cat-eye sunglasses. And if you’re headed to the office on a casual Friday, swap the shoulder bag for a sleek portfolio. 

‍Pro tip: A pair of chunky loafers will balance leggings’ slim silhouette better than an ultra-slim loafer style, especially when you’re adding layers up top. 

 What to look for: Choose lug soles for an edgier vibe, or stick with penny loafers for something more classic. You’ll get the most mileage from neutral shades like black, tan, or camel.

The wrong shoes for leggings: Styles to avoid 

Even Lululemon leggings outfits fall flat when paired with the wrong shoes. Here are four styles to avoid—and what to wear instead.

Platform heels

You might think platform heels are the perfect match for ultra-sleek black leggings—adding that extra height to a leather leggings look is tempting, we know. But while leggings with heels are a solid combo, the chunky silhouette of platform shoes clashes with the bottoms’ slim fit, creating more chaos than contrast. Try heeled sandals or pointed-toe ankle boots for a sleeker match. 

Flip-flops

Unless you’re headed to the shower at the gym, flip-flops with leggings are a fashion no-no. These lazy-day shoes instantly dress down even the most carefully thought-out leggings outfit, making you look more careless than classy. If you’re craving a laid-back look, wear ballet flats or clean white sneakers instead—both are casual yet stylish, pairing comfort with a heavy dose of outfit appeal. 

Sock boots 

These stretchy shoes blend a little too well with leggings, especially when the colors match. The result? A footie-pajama-meets-winter-slipper effect that gives off juvenile energy while flattening your figure. For a more defined shape, try structured combat boots—a great footwear choice for adding edge and contrast to leggings in winter. 

Espadrille wedges

There’s a time and a place for espadrilles, and it’s with linen pants and sundresses, not leggings. The textured soles of these shoes compete with the leggings’ sleek leg line, making the look feel disjointed. Want something breezy but intentional? Try sleek athletic sneakers or low-block heels instead. 

Find cute shoes for leggings on ThredUp

The right shoes will take your leggings outfit from everyday casual to effortlessly elevated. Whether you’re into ankle boots, stylish sneakers, or statement heels, ThredUp has the best secondhand shoes to wear with leggings—all at budget-friendly prices. 

ThredUp drops thousands of new arrivals daily, making it easy to refresh your closet sustainably. Need a little fashion inspiration? Our Style Chat feature helps you brainstorm outfit ideas, explore trends, and preview complete looks before you buy. 

‍Browse ThredUp today to find the perfect shoes to wear with your favorite leggings.

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