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The 14 Best Shoes To Wear With Leggings
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Leggings are a versatile wardrobe staple that can take you from a morning yoga class through your day at the office and out to dinner afterward, but finding the right shoes to go with them can be surprisingly tricky. The best shoes to wear with leggings are easy to style, comfortable (because that’s why you’re wearing leggings in the first place), cute, and have durable outsoles made from rubber or TPU that can stand up to regular wear.
What To Look For In A Pair Of Shoes For Leggings
The first thing you’ll want to think about is when and where you tend to wear your leggings. If you’re going to and from workouts, a pair of sleek modern sneakers, chic platform sandals, or sporty slip-on shoes are all great choices since they’re comfortable and look great with athleisure outfits. If you love to rock your leggings with chunky sweaters and flannel shirts in the cooler months, look for knee-high boots in genuine or faux leather for a timeless style. Ballet flats and loafers are good options for those days when you need to look a little more dressed up but still want to wear something comfortable. And on rainy days, it’s hard to beat the cozy factor of rain boots and leggings.
Whenever you’re shopping for shoes, looking for quality materials should also be a consideration. Outsoles made from rubber or TPU, a type of plastic commonly used for footwear, tend to be sturdy, weather-proof, and anti-slip, which are qualities you want in a shoe. Uppers can be made from breathable textiles, genuine leather, or synthetic leather. They all have their pros and cons, so what you choose really comes down to a combination of your budget and your personal preferences.
However you like to wear your leggings, there’s a pair of shoes for you on this list. From ballet flats with thousands of fans on Amazon to chic ankle boots with chunky heels, keep scrolling to find your new favorite shoes for leggings.
1A Pair Of Chunky Ankle Boots With Thousands Of Fans On Amazon
These inexpensive ankle boots are great for wearing with leggings and a bomber jacket in the cooler months. They have a sleek, minimalist design, chunky 3-inch heels, and synthetic soles. If you’re worried about walking in this heel height, don’t sweat it — reviewers on Amazon noted that for boots this tall, they’re surprisingly comfortable. The uppers are made from soft-touch suede with elastic on both sides of the ankle, so there’s a bit of stretch to the fit. These boots come in seven dark neutrals that are so stylish, you might find yourself wanting to buy multiple pairs.
One fan raved: “LOVE these boots! They look so cute with any outfit. Jeans, a dress or leggings! Not to mention they are so comfortable I can stand in them for hours! Love the rubber bottom. Living in Boston with our horrible winters it’s good to know I have a pair of cute heeled boots that I won’t slip in when it comes to winter weather!”
Colors and styles: 7 | Sizes: 5 — 11
2A Pair Of Fashionable Sneakers
This pair of sneakers not only offers a chic style, but they are great for rounding out the quintessential athleisure look. These Sorel sneakers have durable, bubble-like, rubber soles with a split design, and the uppers are made from a combination of breathable mesh fabric and durable leather. The low-cut style makes them a perfect choice to wear with leggings and an oversize hoodie or T-shirt for an on-trend streetwear look. Plus, they come in 18 colors and styles to choose from.
One fan raved: “These are SO well-designed, 90's trendy, comfortable, yet interesting and innovative! You could wear these with any leggings, anywhere. Fabulous!”
Colors and styles: 18 | Sizes: 5 — 12
3These Basic Ballet Flats That Will Go With Everything In Your Closet
There’s nothing like a pair of ballet flats to make literally any look feel a bit more polished. These flats from Amazon Essentials offer great value at just $17, and they’re backed by over 35,000 five-star ratings on Amazon. Made from 100% synthetic materials, they have a classic round-toe design and are flexible and foldable, so they’re easy to pack or toss in your bag to slip on after work or a workout. The insides are lined with soft microfiber, and there’s a little extra padding around the heel for added comfort.
One fan raved: “So cute! Love them. Can wear with anything from dress to leggings to jeans! Comfortable and worth every penny”
Colors and styles: 35 | Sizes: 5 — 15, including wide sizes
4These Lace-Up Loafers With An Overall 4.8-Star Rating
These supremely comfortable shoes have earned an overall 4.8-star rating and over 33,000 reviews on Amazon, with many reviewers writing that they’re the most comfortable shoes they own. They feature a flexible and soft cotton canvas or linen upper and a spongy and lightweight sole that one reviewer wrote is “like walking on clouds.” These all-season shoes work great with leggings, jeans, and skirts, and they come in a bunch of different colors and patterns to suit your style.
One fan raved: “These shoes are like walking on clouds!! I’m a k-2 special education teacher and I wear Hey Dudes every day to school. I love how I can wear them with jumpsuits, dresses, jeans or leggings and my feet or back don’t hurt at the end of the day. I highly recommend”
Colors and styles: 27 | Sizes: 4 — 11
5Some Loafers That Reviewers Say Are So Comfortable
These basic loafers cost just $26, but they’re worth so much more since reviewers on Amazon agree that they require no break-in period. If you love wearing leggings to work, style these loafers with a basic black pair and a simple sweater or a T-shirt and blazer. They’re made from 100% synthetic materials with a chic, pointed-toe design, and the inner heel is padded for extra comfort and blister prevention. Plus, these shoes have durable TPR outsoles with a low heel that’s comfortable to walk in.
One fan raved: “Pointy toes are just right, adorable with leggings and so much more. It’s rare for me to buy patterned shoes and these are darling.”
Colors and styles: 12 | Sizes: 5 — 15, including wide sizes
6A Pair Of Knee-High Boots That Are Actually Comfortable
The combination of knee-high boots, leggings, and a big blanket scarf is classic for a reason — it looks amazing. These boots from Naturalizer are made from 100% leather with a synthetic sole, and they come in four cozy neutral tones. They have a zip closure, adjustable buckles, and elastic in the shaft, which makes these boots a particularly great choice for those with wider calves. The low heel makes these easy to walk in, too.
One fan raved: “Bought this boot in both dark tan and black; both fit exactly the same...perfectly! leather is of good quality, and heel height is excellent for everyday wear...very comfortable.”
Colors and styles: 4 | Sizes: 4 — 12, including wide and extra-wide sizes
7These Under-$40 Combat Boots That Amazon Shoppers Love
These cheap combat boots are perfect for styling with leggings, a crisp white button-down, and some chunky gold jewelry for a look that’s sophisticated with a bit of an edge. They’re made from 100% synthetic materials, which makes them a solid choice for anyone who wants to avoid wearing leather, and they have rubber outsoles with good tread for all-weather wear. They have a simple lace-up style with a side zipper and come in both brown and black.
One fan raved: “This boots are super duper comfy .. i could care less that they are not real leather.. [...] after throwing on a chunky turtleneck and leggings, out the door i went to experiment.... all i can say is this: fantastic! the more you wear 'em, the better they are. many compliments, and they've turned out to be my absolute fave boots.”
Colors and styles: 4 | Sizes: 5 — 13
8Some Budget-Friendly Canvas Sneakers
A great pair of canvas sneakers is perfect for styling with leggings and a flannel shirt for a 90s-style look. These are just $21, but they’ve still racked up over 22,000 five-star ratings on Amazon from shoppers who say they’re just as good as more expensive versions. The uppers are made from canvas, and the soles are made from nonslip rubber that won’t wear out too quickly. The low-cut, round-toe design makes these an excellent choice for wearing with leggings, and they come in a variety of solid colors and fun patterns.
One fan raved: “Love them! Comfortable, perfect fit- width , toe box, all perfect. Support is average, but I could easily add a simple padded arch support for long outings. So far haven’t needed anything. I wear them with simple maxi dresses, kimonos over T-shirts and jeans, leggings… I will buy another pair in another color”
Colors and styles: 26 | Sizes: 5 — 11
9A Pair Of Slides With Amazing Arch Support
These comfortable platform sandals have two simple leather straps and a 1.75-inch platform heel that makes them look super cute with leggings and tanks or cropped tees in warmer weather. The straps are adjustable thanks to the hook-and-loop closures, and the EVA footbed is covered in soft microfiber that feels amazing against bare feet. They also have Vionic’s signature three-zone comfort design that’s meant to form to the contours of your feet, providing exceptional stability and arch support.
One fan raved: “Very supportive strong sturdy Vionic sandals! [...] True to size. They hug your feet perfectly! Amazing arch & heel support. Super comfortable. Look great - can dress them up too! Can walk for miles in them!”
Colors and styles: 13 | Sizes: 5 — 11
10These Laidback Toms Slip-On Shoes
These classic Toms are perfect for running errands or wearing to and from workout classes, and the simple loafer-like design works well with a casual legging and T-shirt (or cozy sweater, if it’s chilly) ensemble. The uppers are made from 100% canvas, so they’re super breathable and great for year-round wear. They also feature a durable rubber sole that offers good traction on any surface. Popular on Amazon, these shoes have over 22,000 five-star ratings.
One fan raved: “Tom's are forever and always my favorite casual shoe. I'm on my 3rd pair because they are the most comfortable and easy to wear shoes that I have purchased.”
Colors and styles: 233 | Sizes: 5 — 14, including wide sizes
11Some Cute Wellington Boots For Rainy Days
It’s hard to beat the original Hunter boots on rainy days. These tall rain boots are made entirely from latex and rubber, so every inch is waterproof, meaning you can trudge through puddles, mud, and whatever else nature sends your way without a worry. They have a low heel that’s just over an inch tall, and a 16-inch shaft that hits a bit below the knee on most wearers. They come in both glossy and matte finishes, as well as a variety of fun colors. Snag these in a color that matches your raincoat, then pair them with leggings for a look that’s cozy and cute.
One fan raved: “I like the green boots the best, I find them fun and look great with jeans and black leggings [...] If they were good enough for Lady Di then that is all I need as an endorsement :)”
Colors and styles: 23 | Sizes: 5 — 13
12These Knee-High Boots With A Soft Faux-Fur Lining
Want some inexpensive tall boots? Try these motorcycle boots, which are perfect worn with your favorite pair of black leggings, a black tee, and a black leather jacket for a monochromatic look that you can wear just about anywhere. They have a low 1.25-inch heel that’s comfortable enough for all-day wear, and they’re made from a leather-like material that has a faux-fur lining for warmth and softness. These boots zip up the sides, so they’re easy to put on and take off, and hit just below the knee. They also have rubber outsoles for traction and durability.
One fan raved: “I love those boots. I have received many compliments on them. I love the style and they have a nice,thin fur lining. I wear them with leggings and skinny jeans. They are so comfortable to wear all day and keep my feet and legs warm.”
Colors and styles: 6 | Sizes: 5 — 12
13The Classic Stan Smith Sneakers
Leggings and Stan Smith sneakers are a match made in fashion heaven because of the simple, sporty look, and the crisp, white design makes for a versatile shoe you’ll get a lot of mileage out of. The synthetic uppers are made from a minimum of 50% recycled materials, so buying them isn’t just a style choice — it’s also one that’s good for the planet. These sneakers have durable rubber outsoles and lace-up closure for a classic, secure fit.
One fan raved: “I LOVE these sneaks! They are so comfortable and can be worn with anything! I wore them for walking around all day and there were no issues!”
Colors and styles: 18 | Sizes: 4.5 — 11
14Some Short Rubber Boots You Can Wear In Any Weather
If you prefer short rain boots, these rubber boots can also double as regular Chelsea boots (especially if you get them in a neutral color), making them a versatile addition to your shoe collection. They’re made with a waterproof rubber material and boast stretchy panels on the sides for comfort without sacrificing water resistance. The insoles are removable, so if you don’t like the one they come with, you can easily swap it out for a different one, and the outsoles have deep treads, giving them solid traction, no matter the surface.
One fan raved: “The quality of the product and the affordability of them is a total win! Really happy with this purchase. I definitely will be recommending this product to all my friends because they are the perfect white booties to wear in the rain or even hiking or just leisurely walking around when the weather is mild.”
Colors and styles: 11 | Sizes: 6 — 11
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