10 Best Shoes To Wear With Leggings Reviewed & Rated
Alanna Elia
Team WJR
Okay just admit it…There’s a pair of leggings (or two) hiding somewhere in your closet! They have this miraculous way of looking good with anything you wear. What is it about them that’s just so darn fascinating?! Perhaps it’s how they enhance every curve or hug every contour… Maybe it’s how they look good with practically any outfit? Whatever the reason, the world just can’t seem to get enough!
We carefully researched the hottest kinds of shoes to match these slim-fitted pants and created a guide to the top ten. Keep reading for a detailed description of the ten best shoes to wear with leggings, as well as, a breakdown of the criteria used to evaluate each one. We’ve even included answers to some of the most frequently asked questions on the topic to bring you the most complete guide possible.
In a Hurry? The test winner after 13 hrs of research
Genuine Leather Upper
Glove Leather Lining
Cushioned Insole
Antimicrobial Treatment
Handcrafted
Top 10 Shoes to Wear With Leggings
1. Thursday Boot Company Captain
Genuine Leather Upper
Glove Leather Lining
Cushioned Insole
Antimicrobial Treatment
Handcrafted
Runs Small
Lower Quality Than Men’s Style
To be honest, this isn’t a boot that’s only good to wear with leggings - it’s questionably the best boot you will ever own. Made by a reputable brand, the Captain is a classic style that goes with anything, from skinny jeans to leggings, to skirts and dresses, this will look just at place at the office, or during Sunday brunch with your friends. Available in a number of colors, as well as a leather and suede option, you can get the version that matches your wardrobe best, and enjoy a style you’ll be wearing for years. Check out other details below about these shoes to wear with leggings.
Read moreCushioned
The sole of this boot features shock absorbing cushioning that’ll beat fatigue even when you’re standing or walking for several hours. It also features an antimicrobial insole that won’t develop odors, making these the perfect fall boots.
Genuine Leather
The upper of the Captain is made with Chrome Leather, while the inside is lined with full glove interior lining, allowing you to get the perfect fit after just a short break in period. Being made with natural materials, this model will also allow a good amount of airflow to the feet.
Cost and Value
Though slightly higher in price than the average boot, this model is a great investment for those who want something that both looks stylish and is comfortable for daily wear. It’s quite easy to keep clean, and has been handcrafted, so you can rest assured you’re getting a premium product.
2. Timberland Earthkeepers Glancy
Chunky Heel
Textured Rubber
Lugged Outsole
Lace-Up
Sizes Run Small
Timberlands Glancy is a gorgeous pair of shoes to wear with leggings. They offer a full-grain leather upper and a lightweight synthetic outsole for complete, whole-foot comfort. It’s six-inch shaft and padded collar make for an enjoyable ride that will keep you coming back for more. A chunky three-inch heel adds some serious lift while still allowing for a natural stride. These boots are perfect to wear with stretch pants and are sure to fast become your favorite go-to pair.
Read moreTextured Rubber Heel
Timberlands’ Glancy features a textured rubber heel and sole that is extra durable and can withstand tough wear and tear. The rubber is made from 15% recycled material for an eco-friendly option. It's 5.5-inch shaft and three-inch heel height are comfortable for walking in and make these a great pair of boots for any season.
OrthoLite Footbed
An OrthoLite footbed offers the ideal amount of cushioned support for a comfortable all day experience. Ortholite provides an ideal level of cushion that's supple enough to protect the delicate underside of the foot while still offering a firm structure that supports and cradles the arch of the foot. Wearing a pair with inadequate support puts you at risk of arch collapse and other painful conditions which is why proper supportive footwear is so important.
Cost and Value
These boots Are a bit more costly than some of the options on the list but they're certainly a worthwhile investment. Their oh-so-stylish design and comforting structure are perfect for busy ladies on the go who want to look their best while they're on the move. You'll enjoy matching these with your go-to pair of legwear and will look super-hot doing so.
3. Dr. Martens 1460
Air-cushioned Sole
Slip Resistant
Durable
Ankle Stability
Goodyear Welt
Vegan Options Available
Heavy
Long Break In Period
The iconic book that was originally designed for workers who needed heavyweight, protective footwear that would be comfortable enough for all day wear, and durable so that it would provide good value has become a staple in almost anyone’s closet. Not only is it popular in mainstream fashion, it’s been appropriated by a number of subcultures, and has come to be available in such a huge variety of color options that you can safely pair it with anything, and look amazing and unique.
Read moreOutsole
The best part of the 1460 is the air cushioned rubber outsole that’s oil, slip and abrasion resistant, and has that iconic yellow color that’ll definitely draw attention to your footwear - in a good way. Made with a Goodyear welt, it’ll keep its integrity through the years and even protect you from rain.
Upper
As mentioned, the 1460 comes in a variety of uppers, so you really can choose the perfect version (or versions) for yourself. From black leather, to vegan materials, to glittery textile and flowery prints - anything’s an option with these boots.
Cost and Value
This is probably the best investment out of all of the models on this list. While the price is slightly higher than average, this is a product that’ll serve you for years, while taking care of it should be relatively easy. Furthermore, it’ll protect you from slips and falls, and shouldn’t soak through in rainy conditions, which are great features for all year wear.
4. Converse All Star High Top
Athletic Sneaker
Lace-Up
Metal Eyelets
Rubber Outsole
Higher Price
The Chuck Taylor All Star from Converse high top sneaker that's as Ledic by Design. It features a breathable canvas upper unit and metal eyelet lacing system for a secure and stay-put wear. This pair has been a favorite among wearers for decades and with good reason! Anyone searching for a low-key and casual option to match with their form-fitting legwear will absolutely love these comfortable kicks!
Read moreUnisex
These sneakers are made for everyone to enjoy! They are unisex by design which means guys and gals can share in the love. These athletic Converse sneakers are super-cute and look great with a skinny ankle pair of pants thanks to their high-top structure that distracts from the size of the foot and looks sporty and laid-back.
Breathable
This pair of footwear is made for comfort and features a breathable canvas upper unit that allows for adequate airflow around the foot. When you’re feet don’t have proper airflow they sweat excessively which leads to a build-up of odor-causing bacteria. This is why having a pair that keeps you cool and dry is so important.
Cost and Value
These shoes to wear with leggings cost a little more than some on the list, but they’re certainly worth it! Converse has been a trusted name in fashion footwear for decades and delivers quality options time after time. Go ahead and let your athletic side run wild while wearing these comforting and performance-geared kicks.
5. TOMS Classic
Canvas Upper
Lightweight
Cushioned Outsole
Elastic Gore
Beware of Counterfeit Items
Break-in Period
The go to shoe for millions of people, the Classic by TOMS is a slip on that feels like a slipper but provides all the benefits of athletic footwear. Having become famous in the past decade, this is one of those styles that comes in a huge variety of colors and prints, from down-to-Earth navy or black, to fun prints inspired by Disney, to lacy designs that are pretty enough to wear as your wedding shoes.
Read morePerfect Fit
When you first purchase a pair of TOMS, you’ll notice that they fit a bit snug, but that will quickly change. Made from canvas, these shoes will mold perfectly to the shape of your foot, allowing easy on and off through the elastic gore at the top. They’re the perfect shoe to put on while you’re in a hurry.
Lightweight
Being made with canvas and a sole that is a compound of rubber and EVA foam, the TOMS Classics is an incredibly lightweight pair of footwear you can easily pack for a trip abroad. It’s also suitable for long walks, not just because it’s cushioned, but also because it won’t weigh you down or cause fatigue.
Cost and Value
With a price that’s average, this is the perfect shoe for almost all budgets. You get a number of style options, and can even forego the suede insole for a vegan version in case that’s something you’re concerned with. Do note, however, that this is mainly a summer shoe and won’t work well in wet conditions.
6. UGG Classic Short II
Water and Stain Repellent
Genuine Sheepskin Upper
Wool Lining
Removable Insole
Lightweight Rubber Outsole
Unsuitable for Professional Wear
Too Warm for Summer
There’s hardly a pair of footwear more comfortable than UGGs. Whether you wear them around the house, to school, on casual outings or while running errands, you’ve probably fallen head over heels with them thanks to the soft materials, perfectly cut upper and warm wool lining. Add to that the 8 different color options, and you’ve got a winner style for a no fuss look.
Read moreImproved Upper
The twinface sheepskin and suede upper received an update with the second version of this boot, and can now repel water and stains, making these easier to take care of, and able to stay looking brand new for longer.
Insulation
These are ideal in cold weather, but won’t have you overheating in spring or fall either - the natural wool used is a breathable material that lets moisture escape while keeping you at a comfortable temperature throughout the year.
Cost and Value
UGGs cost a pretty penny, but considering the materials used, the fact that they’re incredibly comfy and cushioned, as well as the fact that they’ve become a style staple makes them a great choice of casual footwear. Add to this the fact that they come in a variety of colors, and you’ve got yourself the perfect pair of boots to put on while you’re on the way to the yoga studio.
7. Bearpaw Tama 2
Fluffy Pompom Accents
Suede Banded Trim
Sheepskin Lining
9" Shaft
Runs 1/2 Size Small
This comforting pair is lined with Sheepskin for an extra warm experience! Their gorgeous and fluffy exterior is the perfect match for leg-hugging clothes and is sure to demand attention when you walk past. The Tama has a nine-inch shaft that extends up the calf for a snug and stylish design that’s ideal for those chilly Fall and Winter nights.
Read moreSheepskin Lining
Sheepskin is incredibly soft against your skin and provides an extremely comforting environment for your feet. Snow and freezing air will be no match for these winter-ready boots that look as good as they feel. This pair was made to wear with legwear and offers the most awe-inspiring style.
Suede Banded Trim
The Tama features suede banded trim that helps this pair stay perfectly in place all throughout the day. It boasts cord ties that allow for an adjustable wear and super-cute pompom accents! These fluffy pom poms bounce with every step for an unbeatable and original style.
Cost and Value
While they cost a bit more than most of the pairs on this list, they’re certainly worth it! This boot is the ideal choice for fall and winter, while there’s no pair that would look better with skin-tight legwear!
8. Reebok Princess
Lace-Up
Athletic Sneaker
Rubber Sole
EVA Footbed
Fit Narrow
This super cute and classic sneaker is the perfect pair to match with your favorite leggings. It's made from synthetic leather and features a non-slip rubber outsole to keep you steady on your feet. The Princess has a die-cut EVA insole and padded foam sockliner for a completely comfortable wear. Its lace-up design allows for a secure fit, while perforated accents and a side inset logo make this a totally stylish option.
Read moreLightweight Cushioning
The Reebok Princess boasts a super lightweight insole that keeps you walking comfortably for hours on end. Its padded foam sockliner provides an additional layer of padding for superior comfort, while the sockliner also works to absorb excess moisture. This prevents a buildup of sweat and odor-causing bacteria to keep your feet cool and dry for an enjoyable wear.
Rubber Outsole
This pair features a high abrasion rubber outsole that's perfect for walking on any surface. No matter if the weather outside is wet and slippery you'll be secure on your feet thanks to this solid shoe that’s made to help you maneuver with ease.
Cost and Value
These Reeboks are very affordable and offer great value for their price. Anyone who's looking for a super cute sneaker to match with their favorite skin-hugging pants will enjoy the Princesses design. Walk in style and total comfort thanks to this classic and all-inspiring Reebok shoe.
9. Blowfish Balla Wedge
Peep Toe
Open Sides
20 Color Choices
Wedge Heel
Sizes Run Small
This pair of wedge sandals is super cute and will look great with a pair of leggings. It's available in over twenty color variations so you'll have no problem matching them with your favorite outfits. They feature a cute gladiator-styled design and open upper concept to keep you cool and comfortable during the warmer weather. An adjustable buckle closure ensures this sandal stays securely in place for non-slip wear even after hours spent on the move.
Read moreSecurity
This sandal offers criss-cross faux leather straps and an adjustable buckle closure for a secure and customized fit. Its side zipper allows for easy on-off wear and makes for a no-fuss design. These sandals are designed with a non-slip outsole and soft fabric insole that feels great against your skin.
Appearance
This pair of Blowfish sandals have a stacked wedge heel that's less than two-inches high so it still allows for easy walking. Its open toe design is very cute and lets you show off your sparkling new pedicure. You'll enjoy the sheer versatility that this pair offers and the multitude of colors there are to choose from.
Cost and Value
These summer sandals are very reasonably priced and are the perfect accessory for any pair of legwear. Go ahead and roam wherever you choose thanks to its comforting footbed and airy upper design that will ensure your feet feel great all day long.
10. Puma Tazon 6
Midfoot Saddle
Lace-Up
Athletic Sneaker
Faux-Leather Upper
Sizes Run Small
The Tazon 6 is a streamlined pair of athletic sneakers that is the perfect match for those skintight leggings! It features a gorgeous synthetic leather upper and non-slip rubber outsole for secure footing on any surface. This stylish pair sports the Puma logo on the tongue as well as along the toes and has statement tonal laces that offset its solid backdrop.
Read moreEcoOrthoLite Sockliner
This sockliner provides the ideal mix of comfort and performance enhancement! It ’s an environmentally friendly and bio-based technology that's also a renewable resource. EcoOrthoLite products naturally provide the perfect level of cushion and support to the delicate underside of the foot, while wicking excess moisture away from the skin.
Midfoot Saddle
This pair of footwear offers a TPU stability shank that helps to cradle and support the delicate underside of the foot. Its mid-foot saddle offers the most comforting wear imaginable while also providing the perfect fit. It's EVA heel counter absorbs the waves of shock which travel through the foot and up the leg with every step you take.
Cost and Value
These shoes offer an incredible value and are jam-packed with top-of-the-line features. They're designed for a completely comfortable wear that’s perfect for those who are on the go from dawn until dusk. Best of all, these sneakers present the ultimate in stylish appearances and will look great with a sleek pair of pants.
Criteria Used for Evaluation
Style
Materials
One of the first things you should look at before purchasing a pair of footwear is the type of materials used for construction. More than just determining the type of use the shoes will be appropriate for, the material can tell you a lot about what you can expect in terms of comfort, durability, maintenance, etc. There’s a huge variety of materials used to manufacture shoes nowadays - from traditional natural materials, to newly developed synthetics and knits that have high-tech features that will help you feel better.
Comfort
More than the looks, what determines a good pair of shoes to wear with leggings (or anything, really), is how it feels on your feet. Because everyone’s foot shape and size is unique, it’s best to keep in mind that what works for one person may be uncomfortable for another. Nonetheless, there are a few points which we all should consider before making a purchase.
Value
The price tag associated with a pair of footwear can often be the deciding factor when it comes to the question whether we’re going to be taking them home at the end of the day. While everyone has a different budget, what’s the same is that all of us want to get the most bang for our buck. For some this may mean the latest designer fashion that’ll make them stand out, while for others, it’s an affordable pair of shoes they can easily wear on a variety of occasions.
If you’re looking for something that’ll be worth the investment, here are a few simple rules to follow while shopping:
Features
Expert Interviews & Opinions
Style Materials Comfort Value Features 
While many on our list are designed for fun, flirty styling when paired with leggings, they aren't the ONLY options out there to try out.
Pairing high heels with leggings may not be the most comfortable for all day wear, but it makes for a sexy evening outfit for date night or dancing!
Leggings have become one of the most popular garments to wear for casual, or formal occasions. Simple black leggings can be worn anywhere, and paired with just about anything for fancy or casual settings. For more playful designs and patterns, leggins with brighter colors or space
Other Factors to Consider
Bottom Line
Leggings are a great, comfortable piece of clothing that can be dressed up or down, and combined with almost any shoe out there. What makes an ideal pair of footwear to wear with them is actually not just one particular style, but what feels right for you. They’ll look just as good with flip flops as they will with pumps or sneakers, so make sure you go with what feels best for you. In addition to that, make sure you follow the most important criteria listed above:
Frequently Asked Questions
q: What exactly are leggings anyways?
They’re a form-fitting pair of stretch pants. They’re thicker than stockings but are usually still quite thin and can often become see through if they’re worn too small. Many people argue that leggings aren’t really pants, though they are classified as such. They can be worn for athletic activities and are very popular for yoga and jogging. A great thing about this style of clothing is that it looks great with practically anything and there are so many colors and styles to choose from.
q: Can I wear a square or pointed toe with them?
It’s best to opt for a rounded toe because any other style runs the risk of making your feet appear larger than they actually are. Rounded toe footwear diminishes the appearance of the foot by giving the illusion of a lesser size. Whereas, elongated shapes make your feet seem larger than they actually are. This is something you generally try to avoid while wearing a pant that has a skinny cuff.
q: Are these kinds of shoes trendy?
These styles never get old! They’ve been a go-to staple for decades and surprisingly, hasn't waned in popularity at all over the years. The pairs featured on this page are all very popular and some are from the biggest names in the footwear industry. The fashion A-listers and celebrities of today are all seen wearing leggings quite regularly because they’re a great choice of apparel. Any brand of footwear can look good with this style of clothing so you can wear super trendy looks if that's what you like. The best choice will detract from the size of the foot itself and will offer a rounded toe. Pairs with accessories like fur trim or hanging pompoms are always super cute with these pants because they help draw attention to the way they hug every curve.
q: How do I keep my shoes clean?
The best way to do this is to follow the manufacturer's instructions. Note that most styles won't be OK if you toss them in the washer, as it's best to be gentle with them and only spot clean.
q: Should I wear socks with them?
This depends entirely on the look you're going for. While sandals definitely shouldn't be worn with socks, other styles can be combined with hosiery for added comfort, or a fashion statement. If the temperature is cold, however, we do recommend wearing socks, as well as a warm pair of boots.
