10 Best Shoes To Wear With Your Leggings

Who doesn’t want to look chic and trendy every time they step out of the house? In fact, as women, we often spend hours trying to figure out how to rock any attire that we don. We often end up buying clothing that we may regret later. So, if you want to look fashionable and yet do not want a burn a hole in your pocket, leggings are your best bet. They have been a staple in the fashion industry for years now and are still quite popular amongst women of all ages.
You may be wondering why buy something as commonplace as leggings when you can buy trendy apparels that are being introduced in the market every day. Well, to answer that in a word would be quite difficult. In fact, the reasons why leggings are a must-have for any women willing to look stylish are many. Let’s find out why leggings are still the favorite of women across the world.

Why Choose to Wear Leggings?

If you have never bought a pair of leggings before, then it can be undoubtedly said that you have missed out a great deal so far. And for those that think that leggings are just good for workouts, you need to give it a second thought. Leggings are a lot more than you think and the following reasons will tell you why:

  • Leggings are one of the most versatile clothing items that you can think of buying. You can wear them on any occasion and at any time. Not only that, but leggings can also be worn all round the year; you just need to choose the correct pair for each season. They are good for formal, semi-formal, as well as casual looks.
  • Leggings can be paired with a variety of outfits and accessories to get the look you that you desire. From a hot, sexy look to a demure, daily look, you can get everything with a pair of leggings matched with suitable apparel and accessories.
  • They are the most comfortable clothing item that you can buy for yourself. Whether you want to be yourself at home or look chic when you step out of home, leggings are what you need.
  • They are very light and are the perfect travel partners if you want to travel light, yet do not want to compromise with your look and style.
  • They can be worn with almost all kinds of shoes to sport different kinds of looks. Naturally, you will be able to wear all your favorite shoes with a pair of leggings.
  • Leggings come very cheaply. That is why you can buy several pairs of them without having worry much about your budget.
  • Leggings fit you’re perfect which means that they will highlight your curves without squeezing your legs. So, you can wear them as long as you want without any issue.
  • Leggings give you super flexibility. From sitting on your couched slumped to shaking a leg at a party, you can do practically anything in a pair of leggings – a benefit that most clothing items cannot provide.
  • If you are into regular workout sessions whether that be at a gym, at home, or outdoors, you will find a pair of leggings to be your savior. You wouldn’t need to invest in expensive gym wear, yet workout as you would like to.
  • For the health-conscious, you wouldn’t need to adjust your pants every time you have a heavy meal. Leggings are quite different from jeans or trousers at the waist and thus, do not put extra pressure on your tummy.

Shoe Types that go well with Leggings

To make leggings work for you for all kinds of occasions, moods, and seasons, it is necessary that you pair them up with the most suitable pair of shoes. If not properly chosen, shoes can make your style look out-dated, blunt, or over-the-top. That is why it is essential that you know what kind of shoes you can wear with your leggings and what makes the best combinations. Here, we will talk about a few of the common shoe types that go well with leggings on different occasions and moods.

Heels: Let’s start off with one of the all-time favorites – heels. Women across age groups like to wear heels and the best part is that they fit great with leggings, especially those that floral prints or animal motifs. Stretchable leathery leggings, too, demand heels to steal the show. 

Loafers: If you want a stylish, smart look, then it is best to team up your leggings with a pair of loafers. These shoes being polished and chic in look ensure that you look sophisticated yet feel comfortable.

Slides: For casual as well as an active look, slides are the best bet with your pair of leggings. They can help you look effortlessly cool and are, thus, an ideal example of the trendy athleisure wear. Pairing them up with a simple tee and an oversized stylish sweater can do the trick for you.

Ankle boots: Who doesn’t love wearing ankle boots? They are super stylish, smart, and comfortable. And when you team them up with the right leggings, they make a pretty fantastic pair. They not only fit well with your standard pair of leggings but also create a hot, trendy look when paired with leather leggings. This makes ankle boots a great match for your favorite pair of leggings.

Sandals: Sandals are easy to wear and no doubt, stylish. But have you ever thought of pairing them up with your leggings? Well, many may feel that sandals won’t go well with leggings, but they do, in fact, look good with leggings. The trick is to find the outfit that will look good on you and you can wear your sandals without being a fashion disaster. Flat sandals make an excellent choice for your daywear while heeled ones are good for evening outings, parties, etc.

Gladiator sandals: These sandals are in trend for a while now and pairing them up with your leggings can create the perfect look for your body shape. Remember to choose a suitable style and height as well as color for your sandals. This is important to make sure that your style ticks off well with the shape of your body.

Ballet flats: You want a no-nonsense, simple look? Try out ballet flats with your leggings. They are simple and comfortable and together with the right pair of leggings, they create the most casual and chic look. The best part is that you can team up this combination with a variety of casual wear such as chambray shirts, sweater dresses, crop top with a leather jacket, etc.

Pumps: Pumps are a great choice to go with leggings. You can choose to wear chunky or wedge-heeled pumps with your leggings. The length of the leggings is very important in this case as the leggings shouldn’t go beyond the pump tops. This look is very easy to pull off and is very stylish as well. However, if you are in the mood for something more bold and retro, wear high-heeled or stiletto pumps with your shiny leggings.

Kneehigh boots: When the chill sets in, it is best to pair up your leggings with knee-high boots. Together, they make the perfect, cozy winter outfit that look stylish with an oversized sweater and a beanie. Leather or suede boots are perfect for this style.

Overtheknee boots: Trying to look stylish when the barometer falls sharply is a difficult job. And if you do not want to look like a sack in bulky winter wear, go for over-the-knee boots with your leggings. This will not only help you be warm and cozy, but also would help to do away with those skinny jeans. Plus, wearing leggings under the long, slim boots is much more comfortable.

Combat boots: For those that love to hit the roads often, combat boots are an absolute favorite. And now you can team up your leggings with your favorite combat boots. The best way to rock the look is to add a touch of feminine with ruffles, florals, pastels, etc. with these thick, sturdy boots. You can also opt for a slip dress or denim skirts/shorts with your combat boots and leggings.

Laceup sneakers: For those willing to sport an athletic look, lace-up sneakers are the best fit with leggings. The shoes go best with athletic leggings and create a smart, stylish look with an athletic feel. Make sure the sneakers are minimal.

Slipon sneakers: If you are not so much into lace-up sneakers, try pairing your leggings with slip-on sneakers. These sneakers are not only super comfy, but also create a more laidback and casual look, unlike their lace-up counterparts. You can wear them while running errands near your house or during weekend outings for a stylish yet relaxed vibe.

Oxford shoes: Leggings are inherently casual. But if you want to make up some of the casualness that leggings add to your attire, it is best to pair them with oxford shoes. These shoes help to dress up your outfit a bit and add formality and bling to your look. A pair of neutral leggings and a formal dress or shirt is the best combination with the oxford shoes.

Flipflops: Flip-flops are comfortable, but aren’t the favorites of many as they are too casual. Well, they are which is why they are often considered inappropriate for most occasions, but they can be easily worn with leggings when you want a casual look or want to hit the beach. To get more chic yet classy look, you can try wearing flat thong sandals instead of plain flip-flops.

How to Choose the Best Shoes to Wear with Leggings?

While choosing the right shoes to wear with your leggings, it is important to consider a few factors that will not only make you stylish, but will also make sure that you can wear them with convenience and ease. Let’s take a look at some of the important deciding factors:

  • Use – The kind of look that you want to sport will also help you determine the kind of shoes that you need to buy. For example, if you would most use the shoes for running or workouts, choose a pair that will suit your needs. If, however, you want to wear them to work or for casual outings, you will need to buy a pair that would suit the occasions the best.
  • Material – The first and most important factor of consideration is the material of make of the shoes that you are planning to buy. A particular pair of shoes may look extremely trendy and stylish, but if it is not made of good quality materials or made of materials that aren’t suitable for you, then buying them would be an unwise decision. The correct choice of material will ensure that your shoes are durable and comfortable. The good news is that you have a variety of materials to choose from like leather, suede, canvas, foam, rubber, mesh, etc.
  • Comfort – If you want your shoes to be comfortable, be sure to check out whether a particular pair will fit you well. What may be good for somebody may not be suitable for you. Before buying a pair, check for features like cushioning, shock absorption, breathability, support, flexibility, etc. so that you feel comfortable every time you wear the shoes.
  • Versatility – If you do not want to buy dozens of pairs o shoes, each for a particular occasion or style, versatility is what you should look for in your shoes. Shoes such as Oxfords, boots, pumps, etc. can be used for casual as well as semi-formal looks when paired with the right clothing and accessories.
  • Embellishments – A variety of shoe styles like boots, pumps, heels, flats, sandals, etc. come with embellishments such as tassels, faux fur, gemstones, rhinestones, buckles, etc. Choosing the appropriate embellishments is not only necessary for the correct style, but also for your fashion statement as well.
  • Durability – If you do not want to go shopping for shoes every month, make sure that you choose shoes that are known for their durability. This will be convenient and cost-effective for you as well.
  • Price – Like any other purchase that you make, the best shoes to wear with leggings should also be within your budget. Buying obnoxiously high-priced shoes isn’t worth it, unless you have brand favoritism.

Best Shoes to Wear with Leggings

With dozens of suitable shoe styles, designs, patterns, etc. it often becomes difficult to choose the best shoes to wear with leggings. Not to worry, as here, we bring to you a list of some of the best shoes that you can pair up with your leggings for various moods and occasions.

1. Skechers Cali Women’s Rumblers Sparkle on Wedge Sandal:

These sandals are completely synthetic but look like they are made of suede. These sandals are lightweight and the designs are perfect to add glamour to your outfits. Unlike other heels, these sandals are quite comfortable to your feet and light weight too. Although these sandals only have black as color options, but they certainly look good with any type of outfit. These fine-looking sandals come with 0.5” of platform and 2.5” of heels. Although the upper part of the sandal is not made out of stretchy material but it comes with great elasticity to enable necessary feet movements.


  • Made out of 100% synthetic material
  • Heel is only 2.5”
  • Uses memory foam
  • You can buy perfect fit size but sometimes you might encounter a miss-fit in case you are unlucky
  • Size options are quite variant and comes with wide fitting as well
  • Truly comfortable that makes it perfect for wearing them for longer duration
  • Comes with insole memory foam


  • Comfortable
  • Bouncy sole
  • Perfect combination of style and comfort
  • Does not hurt your feet at all
  • Great cushioning and insole support
  • According to shoes to wear with leggings reviews Perfect to fit in your summer wardrobe


  • The cut is not that nice
  • You may face a bit of size issues
  • Somewhat slippery
  • The strap might be a bit irritating at times to your feet
  • Comes with zero arch support
  • No way to tighten your strap

2. Timberland Women’s Earthkeepers Glancy:

If you are looking for a stylish boot that can go nicely with your leggings, then this pair of boot from Timberland is the best that you can get. The upper part of this boot is made of leather and the synthetic outsole gives a total comfort to your feet. This boot comes with a padded collar and a 6 inch shaft that makes it perfect for a ride and with a 3 inch heel you can always have a nice natural stride. If you are planning to wear a stretch pant, then these boots are going to be a perfect match.


  • Boot upper is made of premium quality leather
  • Comes with padded collar
  • Durable heel and rubber outsole is of high quality
  • The heel is made out of textured rubber and is made to withstand tough conditions
  • Comfortable while walking and perfect for any season
  • With a soft footbed from OrthoLite, these boots become the best choice for long working days
  • Comes with underside cushioning that protects your foot while the firm structure offers you the best support
  • Comparatively these boots might seem a bit costly, but if you think about the value that you get, especially the comfort, design and the structure, you can surely choose these boots to add to your collection.


  • Quite a chunky heel
  • Heel is made of textured rubber
  • Lace Up
  • Synthetic outsole


  • For some customers size has been a problem
  • A bit costly compared to other products available in the market

3. UGG Women’s Classic Short:

If you are looking for a comfortable yet handy pair of footwear then these shoes from UGC is the best that you can get. With a woolen lining, perfectly designed upper and soft materials, you can wear these shoes to school, casual meetings, even in the house and you won’t feel a thing. And when you add the facility to choose from eight different color choices, you can surely look no further than these shoes.


  • Comes with a suede upper and sheepskin that is capable of repelling stain and water
  • Easy to clean, easy to maintain
  • Comes with proper insulation to help you get comfort and warmth during the winter season
  • Although they are quite costly compared to other boots, but if you take into account the materials used, the comfort that you get and the cushioning that comes inside, you can surely choose to add them to your collection
  • Being a casual footwear, it comes with subtle style and with the choice of different colors, it can surely match your requirements any day.


  • Stain and water resistant
  • Upper is made out of genuine Sheepskin
  • Lining is made of high quality wool
  • Insole is removable
  • Outsole is made of rubber that makes it lightweight


  • Unsuitable for Professional Wear
  • Too warm for summer

4. Clarks Women’s Ashland Bubble Slip-On:

Clarks has always been a well-known name in the world of women fashion and this particular product is not an exception either. Perfectly designed with a stylish look, this shoe can definitely be a part of your wardrobe. This shoe is perfect for anyone who wishes to buy a versatile shoe. This shoe is designed with extra-soft leather while the footbed is cushioned with OrthoLite footbed.


  • Quality product at an affordable rate
  • Premium quality leather used for the upper part of the shoe
  • Comes with a small platform and only 1.30” of heel
  • Comes with Cushion Soft Technology that adds to the extra comfort
  • The OrthoLite Footbed provides perfect comfort
  • The outsole is made out of Bendables Technology that gives the shoe perfect flexibility
  • Comes with 4 different width options
  • The upper part of this shoe is really stylish and is made of high quality leather
  • It comes with decorative, flat leather tassels, that adds to the cuteness of the design


  • Classic design to match your wardrobe collection
  • Comes with OrthoLite Footbed for maximum comfort even if you wear your shoes for longer period o time
  • As per the shoes to wear with leggings reviews Exceptionally comfortable
  • Foot support is quite amazing
  • Comes with flexible outsole


  • Have some issues with the size
  • Outsole of this shoe is quite slippery

5. Converse Chuck Taylor All Star Canvas High Top Sneaker:

This all star sneaker from chuck taylor is a perfect example of simple yet stylish shoe. With a high quality and durable rubber sole, and insole cushioning from OrthLite, this is a perfect choice for anyone who wishes to wear a stylish sneaker for all day long. These pair of sneakers are really fashionable, versatile and amazingly comfortable as well.


  • Sole is made of high quality rubber
  • 100% Textile
  • Shaft is only 5.25 inches from the arch’
  • Platform is 1” approximately
  • Lace-up shoes
  • Comes with OrthoLite Cushioning for comfort
  • Upper is made of Canvas
  • Perfectly stylish and well designed to fit versatile wear


  • This is a perfect shoe for those having wide feet
  • Perfect style within your budget
  • This shoe is perfectly designed to match your size and you can wear them all day long
  • Even if you are buying true sized shoe, this will have leave enough space inside for you to wear a sock and you will still have free space inside
  • Perfect shoe to wear during the winter, autumn and spring season
  • Comes with additional leather covering which adds to the insulation during the winter season
  • Comfortable even after wearing socks
  • The exterior of this shoe is made of leather which gives your feet perfect protection against cold, dust and light precipitation
  • You can use a support insole if you would like
  • Although it does not have any arch support, still comfortable enough to wear them throughout the day


  • If you are looking for arch support in your shoe, then this is not the right choice for you
  • As per some users, during the summer, your feet might sweat a lot
  • The soles might not grip the way you think they might

6. Caterpillar Women’s Alexi Combat Boot:

This boot from Alexi is available in three natural colors and with a sweater cuff; this is the best boot that you would like to have. You can easily wear them with leggings and you will look really nice irrespective of the design and color of your leggings. With a comfortable rubber sole and leather lining you can certainly choose to wear these boots on any occasion.


  • Sole is made of rubber which makes it a lot more flexible
  • Comes with leather lining
  • Heal of this boot is only 1”
  • Shaft is about 8” from the arch
  • Comes with stain and water resistant technology
  • Upper is made of Nubuck
  • Front lining is of Nylon Mesh
  • Material used is 10% polyester and 30% acrylic


  • Comes with additional faux far to provide extra cushioning and comfort
  • Lining is made of breathable leather
  • You can fold the top of the boot
  • Enough space to fit in your feet size even if you are wearing socks
  • Available in six different styles to match your requirement


  • According to the shoes to wear with leggings reviews these boots are not really waterproof
  • The customers have complained about the support issues from the manufacturer

7. Clarks Women’s Adriel Viola Dress Pump:

If you have been using Clarks shoes, then you must be well acquainted with the comfort that it brings even with the shoes that comes with heels. This pump shoe from Clark comes with 3” heel but still it does not lack the comfort that you expect from Clarks. This pump comes with rubber sole that adds to the flexibility and the Footbed from OrthoLite provides the perfect cushion that you need.


  • Comfortable rubber sole
  • 100% leather
  • Heel is of maximum 3”
  • Platform is appox 0.5”
  • Comes with comfortable and soft cushion
  • These pumps comes with lining material for extra comfort
  • Comes with OrthoLite Footbed that gives your feet the proper support that it requires


  • Perfectly comfortable compared to other pumps
  • Great heels
  • Inside padding is really soft
  • Comes with rounded toe, chunky heel
  • Slip resistant
  • Heels are flat enough to protect you from falling of the cracks


  • Somewhat loose fit
  • Your feet might slide down if you use nylon socks

8. Havaianas Women’s Slim Floral Sandal Black:

These flip-flops can bring fun, sunshine and vibrancy to your wardrobe. It comes with rice-pattern sole which matches Havaianas sandal style but also comes with additional slip resistant capabilities. These sandals use a secret rubber recipe that makes it a lot more durable and marshmallow soft. With vibrant color options, fashionable designs, these sandals can be perfect match for your beachwear, casual evening wear or swim trunks.


  • 100% soft, durable and high quality rubber
  • Comes with slip proof sole
  • Comes with additional flip-flops
  • Does not lose the shape


  • Comfortable
  • Looks pretty good with leggings
  • Quality material
  • A great buy compared to what you get for the money that you pay


  • Might be a miss fit for your size
  • Quite large to walk

9. Bearpaw Tama 2:

When it comes to choosing a perfect, comforting pair of boot, then choosing this pair of boot from Bearpaw might be the wisest of the options for you. This boot comes with a sheepskin lining for extra comfort and the fluffy and gorgeous exterior makes these boots a perfect match for your choice of leggings. Along with a 9” shaft and a stylish design, this can be perfectly ideal for chilly winter nights.


  • Amazingly soft and extremely comfortable to feet
  • These boots are winter ready to provide you an amazing experience in the snowy weather
  • They not only feel good but also are stylish to match your choice of leggings
  • Even if you wear these boots for whole day, they won’t hurt your feet at all.
  • Comes with fluffy pompoms that adds to its style
  • Comparatively these boots might seem like a bit costly, but they certainly are worth the price
  • As per the shoes to wear with leggings reviews not only these boots are ideal for winter and fall, but also you can wear them as your style wear as well.


  • Fluffy in design
  • Comes with pompom accents
  • Sheepskin lining makes it perfectly warm
  • 9” shaft makes this perfect for winter season


  • A bit costly compared to ordinary pair of boots
  • Might be a bit of misfit depending on the size of your feet

10. Dr.Marten’s Women’s 1460 8-Eye Patent Leather Boots:

These boots from Dr Marten were originally designed for the workers. These boots were designed to provide them with comfort, full protection to their feet and was made to deal with heavy workload. But with the durability, the style statement that it comes with and the color options that are available at your disposal, these boots can surely be the best choice to go with almost anything. According to shoes to wear with leggings reviews it will give you unique and amazing look, especially if you wear them with leggings.


  • Comes with rubber outsole
  • It’s completely slipping, abrasion and oil resistant
  • Available in the yellow color which will surely draw attention to your feet
  • It can last as long as a year and can be a good choice in the rainy season as well.
  • Comes with different upper options to choose from, so you need to choose the one that you need to fit with your outfit
  • Whether you choose to use vegan material, black leather or glittery textile, you can choose anything with these boots.
  • The price of these boots are just higher than any average boots but if you consider the quality, comfort, style statement and of course the capability to match heavy duty, these boots are truly a good buy


  • The outsole is properly Air-Cushioned for ultimate comfort throughout the day
  • Slip resistant
  • High quality material and durable
  • Comes with perfect ankle stability which makes it easier to use throughout the day
  • Does not soak during rainy season


  • A bit heavy compared to other boots
  • According to some users, wearing these boots for a longer period of time is not really feasible

Tips on Wearing Shoes with Leggings

Wearing leggings with your outfits is surely an easy way to get the kind of look that you want. But when pairing your leggings with other clothing items or accessories, it is very important that you follow certain style mantras or you may end up being a fashion disaster. To ensure that nothing such happens to you, here are some style tips for you:

  • Make sure that you choose a size that fits you perfectly. Nothing looks uglier than ill-fitted leggings, however stylish they may be.
  • Choosing the right underwear is very important if you do not want others gaping at you all the time.
  • Solid colors are the best choice for leggings unless of course, you have special something on mind.
  • Tight-fitted or crop tops are a total no-no with tight-fit leggings.
  • It is preferable that you layer your top with something that goes well with your attire.
  • Make sure that your top or your layered clothing covers your hip and preferably, be of mid-thigh length.
  • Choose the length of your leggings according to the style that you want to sport or the shoes that you have chosen.
  • Choose not to wear glossy, leathery, or neon-colored leggings unless you want to don a hot, stylish look.
  • If you are over the age of 40, make sure that you choose leggings that can complement your legs and your look. The choice of length, color, texture, etc. must be carefully done so that you can wear them gracefully anytime.


There is no one best shoes to wear with leggings for everyone. Every person has a different taste, preference, and style and the choice of shoes must be done in such a way that they not only look stylish and feel comfy but also meets the personal needs of the wearer. Make sure that you mull things over very well before clicking on that purchase button.

About the author

Munira Saleh

Hello Readers! I am Munira Saleh, Running The OnlyWomenStuff Blog. Formerly a Teacher, my passion for writing got me into Blogging. I started this blog to provide a platform where i could post all things related to women. I use this medium to create awareness, explore womanhood and share my experience of being a woman; right from Beauty, Fashion and Women’s Health Care to beyond. Connect with me to know more!

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