Our love for leggings has always been strong but “the last few years of working from home have provided endless opportunities to figure out which tops and accessories make our go-to Lululemons look their best,” says PureWow fashion editor Abby Hepworth. Hepworth adds that one of the many merits of leggings is their versatility, but how you style them is key. “Nine times out of ten, wearing leggings with a shirt that hits just above your hips or higher, like a cropped sweater, will throw your proportions out of whack and do nothing good for your figure,” Hepworth says. “Basically, the only exception is if you’re wearing true workout gear, like a breezy tank or sports bra. So, stick to longer blouses and tunics and save your ‘90s baby tee for another day."
18 Shoes to Wear with Leggings, and Still Look Like You’re Wearing a Complete Outfit
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Meet the Expert
Abby Hepworth is the Fashion Editor of PureWow. From the latest trends to designer gossip, Hepworth is PureWow’s office style expert, always ready to suggest a new accessory or silhouette for your lunch date or a story.
The second rule to follow when selecting shoes to wear with leggings is the same one we follow when pairing shoes with dresses or skirts—"the shorter the hemline, the shorter your heel should be, and vice versa,” says Hepworth. “A midi dress looks better with a sizeable heel rather than flats and anything that hits beneath your bum will look better with some block-heeled booties over flat loafers,” she adds. Taking these suggestions to heart and trawling TikTok for additional inspiration, we’ve come up with some great options for shoes to pair with your favorite stretchy pants.
Best Shoes to Wear with Leggings At A Glance
How to Style Shoes to Wear with Leggings
Leggings just might be the most versatile wardrobe piece in your closet, as evidenced by how many different footwear styles look great with them. Sneakers are a great example and can be paired with leggings without looking like you’re about to hit the trails.
On the dressier end of the style spectrum, an over-the-knee suede boot (plus a Chanel jacket) turns leggings from everyday to elegant.
Finally, loafers, square-toe sandals and even Dr. Martens boots are all candidates to rock with your most comfortable leggings.
Best for Collegiate Cool
- Material: woven fabric, rubber outsole
- Colorways: white, blue, yellow
- Sizes: 5 to 12
These chunky-soled, air-cushioned sneakers look as good with your leggings and hoodies as they do a prairie dress. And if you need to run a quick couple laps around the quad for exercise, they work for that, too.
Best for Split Leggings
- Material: leather upper, rubber sole
- Colorways: black, bordeaux, silver foil
- Sizes: 5 to 12
“Beautiful loafers, not too chunky, dresses up any outfit,” says one reviewer. We recommend wearing these with a split-leg legging, so the lug sole adds a lift and allows the legging to hang more elegantly. The black colorway is a classic, while the deeper bordeaux is great for fall. Additionally—and this is a real consideration with any leg-hugging pant—the pointy toe makes legs look longer.
Great for Office Style
- Materials: upper smooth leather, synthetic sole
- Colorways: black, cognac
- Sizes: 5 to 11
Aldo is known for its comfort, and this oxford has lex technology strategically placed at the forefoot of the outsole and insole, so the shoe gives you less resistance as you move. Soft rubber adds traction to the soles for less slipping, and there’s a reinforced heel for added support. Pair these shoes with leggings and an oversized blazer and you’ll totally look the part of a creative professional.
Cushy Ballet Flats
- Materials: woven leather upper, non-slip rubber sole
- Colorways: black, tan, gold
- Sizes: 5 to 12
The pointy toe of this cushiony ballet flat elongates your legs, and the woven leather looks way more expensive than these shoes are. We appreciate how the rubber sole is textured, so no slipping on cement as is often the case with other ballet flats, and the seven layers of padding in the footbed really make a difference when you’re on your feet for hours.
Top Casual Sandal
- Materials: vegan leather, neoprene, outsole is BIO EVA derived from sugarcane
- Colorways: 17 leathers and faux shearline
- Sizes: whole sizes 6 to 12
The slippers-as-streetwear trend is classic now, but we prefer to elevate the look with sleek puffy vegan leather slides that have a bit of heft to them, so they don’t look like you’re actually wearing slippers to lunch. And the puffy straps are filled with memory foam, so walking in them feels like a dream.
- Materials: leather upper with goldtone horsebit, leather lining and sole
- Colorways: white and black
- Sizes: 34 (4) to 42 (12)
“They are so comfortable! [And they] look great with jeans or dresses or even leggings,” writes one reviewer, who bought one size larger than usual for the perfect fit. Italian-made, these slip-on shoes are padded and comfy straight out of the box. And the tapered toe is very on-trend and flattering.
Tops for Sightseeing
- Materials: nubuck and man-made upper, foam footbed, synthetic outsole, elastic straps
- Colorways: black
- Sizes: 5.5 to 11, medium and wide widths
“These shoes are so comfortable and cute! They have a small wedge, so they are not completely flat,” writes one reviewer. These get top marks for sightseeing because the toes are enclosed, which is a great safety feature for clomping around cobblestoned streets (as well as a great way to hide a chipped pedicure). Though the heels are enclosed, the sides are open, espadrille-style, and the straps are stretchy, so they stay comfortable as your foot expands throughout the day.
Maximum Beach Vibes
- Materials: EVA, cotton drill fabric, gummed rubber outsole
- Colorways: 11 black, white and blue colorways
- Sizes: 5 to 17.5
“Cute, comfy, and classic. They look great with jeans, leggings, and skirts,” according to one reviewer. “I like to wear them with the Vans no-show socks. So comfy I can even wear them to work. Love these shoes.” A padded collar and footbed adds to their comfort, and the black-and-white checked design work add a little spunk to plain leggings, and offer a complementarily clash to print leggings. And the slip-on design is the ultimate in get-out-the-door-fast ease.
- Materials: wood, leather
- Colorways: multi-colored leather
- Sizes: 4 to 13
Want to draw as much attention to your feet as possible? These funky leather slingback clogs have mismatched bi-color straps and footbeds that are sure to get you a ton of compliments. We see these with colorful leggings-and-top sets or an all-black or all-white outfit.
Top Rugged Vibes
- Materials: chunky air-cushioned outsole is made from oil, fat, acid, petrol, alkali; smooth leather; tonal metal lace eyes and metallic zip closure
- Colorways: black
- Sizes: 5 to 12
These classic boots have a leg up on the traditional Dr. Martens because they’re designed with an easy to put on zipper on the inside of each boot’s nine-inch shaft. The sturdy soles allow you to bound over puddles and snow drifts confidently, so your feet stay protected from any weather or hazards. And the nine-inch height shaft is made to tuck the bottom of your leggings into.
Best for Hiking
- Materials: suede, textile, rubber, polyurethane
- Colorways: dark grey/salmon laces, golden oak/sage brush laces
- Sizes: 6 to 10
“If you have high arches and need ankle support, these are for you! I have tried a bunch of brands and Danners are the only shoes that work for me,” writes one wearer. “Comfy out of the box and I can hike over pretty much any terrain without slipping.” These are the rare hiking boots that are technically superior—they’re waterproof and the sole can withstand snow or muddy slush without getting your feet soggy—but also brunch-cute, thanks to the brushed suede exterior and contrast laces.
- Materials: leather upper, shock-absorbing footbed, elastic sides, TPU (thermoplastic polyurethane) sole
- Colorways: brown
- Sizes: 6 to 11
Kate Middleton wears hers with skinny jeans and dresses, but the entirety of hipster Brooklyn wears their Blundstone Chelsea boots with leggings. These iconic Australian shoes feature pull-tabs, which make them easy to pull on for a quick dog-walk, while the double-stitching and quality leather just gets comfier and better-looking the more you wear them. “Once broken in, [they’re] very comfy for everyday walking and for low-intensity hiking!” says one reviewer.
The Waterproof Pick
- Materials: rubber upper and sole, textile lining
- Colorways: green, black
- Sizes: 5 to 10
The one-inch heel and 10-inch boot shaft make these waterproof classics a flattering way to balance the proportions of your leggings and bulky sweaters. And the adjustable calf strap loosens from 14 to 17 inches, which ensures maximum comfort and the best fit no matter how bulky your socks are.
The Casual Classic
- Materials: canvas, rubber
- Colorways: 13 colors including customization options
- Sizes: 5 to 15, standard and wide options
“These are maybe my favorite shoes. The off-white goes with everything, and you can walk for miles in ‘em. I will forever have a pair in my closet,” writes Chucks high-tops fan Maggie. Though these shoes were created over 100 years ago for basketball players, the design has largely stayed the same. Thanks to their comfort, style and just plain coolness, they pair well with another classic athleisure staple: leggings. We especially like a longer shirt with them.
Best Over-the-Knee Boot
- Materials: suede upper, synthetic outsole, stacked block heel
- Colorways: black, chestnut, coffee bean, fawn, garnet, graphite, warm grey
- Sizes: 5.5 to 12
A little bit of suede goes a long way when paired with basic black leggings, and these over-the-knee pull-on suede boots are just the shoe to warm your legs, while turning leggings into a whole outfit. They have a half-inch platform on the front and a three-inch stacked heel, so you’ll get height and longer-looking legs with these, while the stacked style of heel and lightly cushioned footbed means they’re still walkable. Plus, they come in a range of warm suede hues that you can easily match to your coat or favorite sweaters for a seamlessly autumnal look.
- Materials: 100 percent Italian leather
- Colorways: black, bone, taupe, pale pink, almond suede
- Sizes: 5 to 11
Fact: Block heel, square-toe styles and leggings flatter your figure. The blunt toe helps balance out your mile-long stems for a more proportional (and modern) finished look—and these all-leather shoes have a two-inch heel and leather sole for added comfort and support. Plus, the ballet-inspired design is totally on-trend right now.
Best Western Boots
- Materials: leather
- Colorways: black, blue, bronze, white
- Sizes: 6 to 11
Ankle height cowboy boots with a low heel are a classic choice for anyone who wants to add some casual country style to their otherwise neutral wardrobe. With a pair of leggings, we like how these boots, with their wide top, make calves look trimmer. And the 1.8-inch heel is comfy for hours and hours—even on horseback. Note: Due to the pointy toe box and narrow silhouette, multiple reviewers advise going up one full size when ordering.
Comfiest for Neighborhood Strolls
- Materials: leather upper, genuine shearling lining, synthetic sole
- Colorways: chocolate, chestnut, grey, black, burnt cedar
- Sizes: 5 to 10
This classic Australian boot is a pioneer in the so-ugly-it’s-cool footwear race. The suede comes pre-treated to protect against stains and other outdoor hazards, and while the boots aren’t waterproof, they’re plenty sturdy and cozy. The unofficial boot of lazy fall afternoons and winter Sundays, we love the look of leggings tucked into these.
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