Best Side Zipper Boots Reviewed

This super handy marvel was created in 1851, but it was only shown to the public in 1893 and has since been improving our lives. Whatever needs to be closed and secured, the zipper has it covered! No wonder shoemakers realized that this innovation was a simple solution to the troubles many people experienced. The placement of the zipper helps a lot too - if it were placed on the front, or on the back, you would probably have more trouble closing it. Shoes with back zippers do exist, but they usually pose a problem and are stubborn, refusing to close down. So, if you need a pair with a side zipper in your dresser, look no further, we’ve got you covered! Our comprehensive guide features plenty of different models with this helpful feature, so you’ll have plenty to choose from!

Standout Picks

Lane Boots Julie
If you truly love everything about Western culture, and would gladly wear clothes inspired by this era, then do not skip out on the Julie boots! These honey boots are 100% leather, soft enough to give your feet a break, but hardy enough to last a lifetime. These boots are completely handcrafted, so every detail was painstakingly put together and thoroughly checked for fallacies, to bring you the absolute best boot they could. The front of the boot is higher than the back, elongating your legs, and making it easy for your knees to bend properly.
Amazon Link
Steve Madden Parkson
This essential style effortlessly combines formal elements with casual tones, making this the ideal versatile boot. The lace-up design makes it easy to adjust the fit, and once you do, turn to the zipper and enjoy an optimal fit every time you put them on. The thick stitch running along the upper determines them as a cap toe, something every sharply dressed person needs in their closet.
Amazon Link
Sudini Fabiana
This polished riding boot combines leather and rubber to bring you the ideal autumn style. The gleaming leather upper flexes and stretches as you walk, and keeps your legs safe in its embrace. They might seem like your regular riding boots when viewed from the front, but once you start to turn them around the quilted stretch back will surely be a shocker. This stretchy back gives an urban vibe to the boot while giving enough room for the widest of calves. The metallic rand combined with the metallic zipper makes these boots ideal for a city setting.
Amazon Link
JSlides Allie
How much do you love sneakers and their casual style? If you can’t imagine going one day without them, don’t freeze in the cold winter days - give the Allie a try! Their sneaker look keeps your casual heart happy, and they keep you warm and toasty. The upper is suede that comes from sheep, hardy and valuable, colored in various shades and patterns. The lack of details give it a refined look, but there is a little stitch that runs along the middle. What could that stitch be?
Amazon Link
Dr Martens Vonda
No boot list would be truly complete without the iconic Doc Martens showing up at least once, and the Vonda is here to show us why. The classic tall doc boot was reimagined as graceful, with a garden of roses blooming all across the upper. The crimson red threads blend with the lively green leaves and are accentuated by the perfectly black backdrop. The black backdrop is top quality leather, checked for mistakes and aberrations by very insightful eyes.
Amazon Link
Rockport Cobb Hill Caroline
The Caroline is a fitting companion for all city dwellers around the globe. The upper comes in leather or suede, in two gentle hues and a vibrant, rusted down red. The stone suede upper also has rustic details, camouflaging them with the rest of your urban companions. Two thick straps crisscross around your ankles, keep you strapped in and give you sharp form.
Amazon Link
Sam Edelman Petty
This iconic Sam Edelman bootie finds its way onto our feet and into our hearts time and time again. One of the best things about it is the variety of colors, materials, and patterns it comes in! If you dislike leather, you can always go with suede, and if you feel pain for animals, why not choose the fabric ones? Sleek, clean uppers work great for business surroundings, while the ones with animal prints and glamorous patterns are simply made to be worn to a gala event.
Amazon Link
Cole Haan Harrington
It’s very obvious here that the zipper was not meant to be hidden! The casual ankle booties sport a chunky zipper colored in brilliant gold, with a lovely tassel detail hanging on the sides, jumping and dancing as you walk. A brilliant attention grab! Their supple upper is suede, a soft and luxurious material that is renowned for its undeniable style. It’s also quite pliable, so you’ll have a cozy experience all around. The slouchy detail contrast the clean upper and gives them drama! Decorative stitching runs along the edges, and a handy pull tab rests on top of the heel counter.
Amazon Link
Fly London Yip
This chunky ankle bootie just begs to see the light of day, as it will keep you warm and classy without any effort. Every detail here is leather, meant to mold perfectly to the shape of your feet, making it easy to forget you actually have any shoes on. No decorations grace the upper, besides the rouched up waves and a metallic instep zipper on the side.
Amazon Link
Naturalizer Jessie
Naturalizer is a company known for creating comfort footwear, and the Jessie is no exception. Their riding boot silhouette is enhanced by the buckle details - two thin ones wrapped around your calves, and a thick strong one resting on top of your ankles. Their upper is leather, made to keep you warm and cozy. Coming in calm, earthy tones, there won’t be a single clothing combination you won’t be able to work them in.
Amazon Link

Criteria Used for Evaluation

Comfort

When you’ve got a long strip of metal hanging by the sides of your shoes, it’s only logical to wonder whether or not those shoes will be comfortable in the first place. Besides being a convenience, since it takes much less time to just slide into your boot and zip it than to lace it, zippers also offer a better fit. When you lace-up your boots, there’s always the possibility that you have either overdone it or didn’t do it quite well, so you end up with a shoe that fits either too tightly or is too loose. And a lot of problems can arise from both!

Loose shoes can create blisters since your feet will move around and create friction, which can open up your skin quite fast. And you don’t have that much stability or balance, so you might injure yourself easier too. On the other hand, tight shoes create corns, calluses, bunions and a whole lot of other issues, which can be painful, unsightly and long lasting! So you’re doing your feet a favor by getting a pair with a zipper on the side.

The other question that might be hanging around your thoughts is, won’t that zipper cause a lot of discomfort for me on the inside? Well, think about it this way: zippers were made for convenience, so why would anyone bother with it if it weren’t comfortable in the first place? If you own a pair of side zipper boots, grab them and inspect the boot from the inside. Close the zipper and open it up; when the zipper is closed up, can you see it from the inside? Of course not!

Shoemakers care about how we feel, and our health, so they devised ways to protect us from the cold kiss of metal. An extra strip of material usually hides the teeth of the zippers, and it doesn’t let it come near our skin. Hardy stitches keep it in place, and if the zipper is good, you can tug it as much as you like, without risking tearing it away from the upper. Also, if you feel cramped up and stuffy there, you can always simply slide the zipper down and let your feet stretch and breathe!

Durability

Yes, zippers are handy, but how hardy are they? We’ve all had experience with zippers that give in after just a few uses, or zippers that pull on the surrounding materials, zippers that break off… Also, zippers can get stuck, or the teeth get broken and so on and so forth. Is investing in a boot with zippers a smart idea? Is there a way to fix all of this?

First things first, buy zippers that you know have quality. Plastic zippers are cheap, but they will break off in no time, especially if you pull on them like there is no tomorrow. Metal zippers are better, but there are still plenty of zippers being cheaply made every day, and it’s important to pick out the best ones. The YKK group, from Japan, creates the best zippers out there, so if you manage to find some made by this particular manufacturer, splurge! You’ll be in good hands.

But what if you’ve already bought a pair with cheaply made bonds and you don’t feel like going out and buying new boots just because of that one simple, yet crucial, detail? If your zipper keeps getting stuck, and you can’t convince it to come down, there are a few things you can try before going to the cobbler. Surprisingly enough, sometimes there is a super simple fix to this: a graphite pencil! Just rub the tip of the pencil on the teeth until it loosens, and if that doesn’t work, lip balm and soap work great too.

Lip balm and soap are especially helpful if the zipper keeps getting stuck in the fabric, or if it won’t close down! If it keeps getting opened, check the teeth - loose threads prevent them from clasping down, and teeth that don’t sit the right way can be troublesome too. Nothing a pair of pliers can’t fix! If the zipper can be closed up when you’re not wearing the boots, but it doesn’t want to hold it together when the boots are on your legs, then they must see the cobbler - you can’t just get a key ring and hook it around the button like you would with jeans! Of course, sometimes the teeth are top notch, but the pull gets broken - there is a simple fix to this though. Just get something that can fit through the little hole and that is strong enough (and that looks good enough), so you can keep using it like normal.

Weather Resistance

Zippers are all good and everything, but how protective are they? Will water break through them and invade your shoes? Do they insulate well enough to keep you warm at all times? Or, do they offer enough breathability?

First things first, let’s talk about water resistance. The teeth of the zippers seem loose enough to let water through, and they might just do that if it was poorly made. High-quality zippers offer enough protection from water, so you don’t have to worry about any type of liquid wiggling itself in. But what about that cloth on the sides? Well, you can waterproof that little part the same way you would waterproof other materials... With a protective spray!

There are many protective sprays out there, and some protection from more than just water. Apply the coat as many times as possible (don’t overdo it), and let it dry completely, and you’ll be protected. If you worry this is not enough, you can always buy already waterproofed zippers or whole boots, or you can buy sealants, that companies like YKK offer.

Since we’re talking about boots here, it’s important they keep you warm and looking good. You can’t be your best if your feet are freezing off! So, do zippers insulate? Yes, indeed they do! There is no reason to worry about all that precious heat escaping, since all the materials surrounding it work together to keep you toasty. The zipper is not a liability, and it won’t let the cold in. Just look at the boots made for hiking - plenty of them sport side zippers! But, zippers won’t let air circulate either, so don’t rely on them to offer airflow. The rest of the boot will do that since shoemakers know how to make a boot with proper circulation. If you’re feeling stuffed up though, there is one simple solution: just slide that zipper down and let all that fresh air in!

Style

Zippers look great on boots made to look rugged, but what if we don’t want to look that way? Can you look stylish while having that convenience zippers offer at the same time? Truth be told, boots that have no zippers will always look clean and polished, while a zipper can be a distracting detail. So, if you truly want to have a shoe that is sleek, maybe opt for ones without a zipper. But who’s to say that a zipper can’t be a good detail too? Many zippers have beautiful pull tabs, and they can really improve the way a shoe looks. Crystals, bold colors, hanging details can all be worked into the way a pair looks and can aid your style.

If you really don’t like the way they look though, well, there’s a reason they sit on the side. They usually sit on the inner side of the shoe, hidden by our feet and the shoe itself. This way, it won’t ruin the look too much, and it will be invisible. The color of the zipper usually matches the color of the uppers too, so they can rarely be seen. You can’t exactly use invisible zippers on shoes, since they would rub your feet, so manufacturers tried every possible way to hide them, for people who don’t like to see them. But, there is no need to obsess about this - it’s better to own a super classy tall boot with a zipper, than to be left without one at all! Zippers can look sexy too, especially if matched black uppers or hot reds. Trust us, no one will notice the metal detail hanging from the sides!

Weight

Boots will always be heavier than your standard sneaker or dress pump. They have much more material on them, added construction details to make them strong, and heels for stability. All of this will add to the weight of the shoe, and we haven’t even mentioned the materials they can be made out of! Leather is a great material, but it’s very heavy, so maybe leather thigh highs won’t be such a good idea, no matter how great they look. If you worry zippers might add to the overall weight, you shouldn’t - they never weight more than just a few grams, and they won’t be the sole player in tiring your feet down.

Instead, look at the materials; as we said, leather is heavy, but so is rubber. Wooden heels are bound to pack extra weight, and enough details can add on to the overall weight as well. But, don’t look at heavy shoes and instantly disregard them - you can get used to the weight pretty fast, and you won’t even notice it after a few wears. Also, any shoe that is too light can be just as troublesome as shoes that are too heavy. If a shoe is too light, it means that it doesn’t have the proper construction to support you and remain durable, which is never a good. So, try to find a middle ground here, or try wearing a pair that is a bit on the heavier side, there’s not much that could go wrong!

Top 10 Picks

1. Lane Boots Julie

Where to buy
Amazon Link
Lane Boots Julie
Amazon Link

If you truly love everything about Western culture, and would gladly wear clothes inspired by this era, then do not skip out on the Julie boots! These honey boots are 100% leather, soft enough to give your feet a break, but hardy enough to last a lifetime. These boots are completely handcrafted, so every detail was painstakingly put together and thoroughly checked for fallacies, to bring you the absolute best boot they could. The front of the boot is higher than the back, elongating your legs, and making it easy for your knees to bend properly.

The rustic appearance is slightly contrasted by the tribal embroidery spanning the whole length of the boot. An urban decorative buckle sits on the side, giving them the full riding boots style. Even more, buckles wrap around your ankles, immersing you into the Western world completely. A part of the belt sports an animal print, while the rest slithers proudly with stud scales protecting their surface.

The upturned pointy toes might look constricting, but there’s plenty of room for your toes to stretch and wiggle. A memory foam insole guards you against the impact forces while you walk on the decorated heel, strutting your way downtown. As you walk, a flash of blue shines in the sun - the iconic outsoles give enough grip and traction to keep you going as long as you need to.

Amazon Link

2. Steve Madden Parkson

Where to buy
Amazon Link
Steve Madden Parkson
Amazon Link

This essential style effortlessly combines formal elements with casual tones, making this the ideal versatile boot. The lace-up design makes it easy to adjust the fit, and once you do, turn to the zipper and enjoy an optimal fit every time you put them on. The thick stitch running along the upper determines them as a cap toe, something every sharply dressed person needs in their closet.

The texture difference on the heels pleases the eyes and gives the boots a little flair. A cushion sits around the ankles, negating the possibility of the upper cutting into your delicate skin and causing more trouble than it’s worth. The contrast stitching and burnished toes add glamour and make you a vision of class. The short stacked heel attached to the ribbed outsole balances your gait and gives plenty of arch support.

Amazon Link

3. Sudini Fabiana

Where to buy
Amazon Link
Sudini Fabiana
Amazon Link

This polished riding boot combines leather and rubber to bring you the ideal autumn style. The gleaming leather upper flexes and stretches as you walk, and keeps your legs safe in its embrace. They might seem like your regular riding boots when viewed from the front, but once you start to turn them around the quilted stretch back will surely be a shocker. This stretchy back gives an urban vibe to the boot while giving enough room for the widest of calves. The metallic rand combined with the metallic zipper makes these boots ideal for a city setting.

The linings are leather as well, cushioning your legs and giving them plenty of protection. As you slide your feet in, you will encounter a sock - a removable sock, but don’t be too quick to throw it away just yet! They sport a dual density shock absorbing surface, meaning you will be safe from the dangerous cold, and safe from pain set off by standing or walking around the whole day! The outsoles are lug rubber, a flexible variety of regular rubber that still gives enough grip to make you steady on all sorts of terrain!

Amazon Link

4. JSlides Allie

Where to buy
Amazon Link
JSlides Allie
Amazon Link

How much do you love sneakers and their casual style? If you can’t imagine going one day without them, don’t freeze in the cold winter days - give the Allie a try! Their sneaker look keeps your casual heart happy, and they keep you warm and toasty. The upper is suede that comes from sheep, hardy and valuable, colored in various shades and patterns. The lack of details give it a refined look, but there is a little stitch that runs along the middle. What could that stitch be?

It’s so you can easily turn them inside out, showcasing their beautiful furry linings! This is made even easier by the two golden zippers running along both sides of the boot, making it supremely easy to slide in and out of the boots. The fur linings keep you warm, wick away moisture and make winter seem like a bad dream. A cushioned footbed hugs your feet, while a removable gel insert keeps you pain-free. The chunky white soles iconic for skater sneakers are what completely push them into the casual world. They do bend easily and give enough support for your sensitive joints and muscles.

Amazon Link

5. Dr Martens Vonda

Where to buy
Amazon Link
Dr Martens Vonda
Amazon Link

No boot list would be truly complete without the iconic Doc Martens showing up at least once, and the Vonda is here to show us why. The classic tall doc boot was reimagined as graceful, with a garden of roses blooming all across the upper. The crimson red threads blend with the lively green leaves and are accentuated by the perfectly black backdrop. The black backdrop is top quality leather, checked for mistakes and aberrations by very insightful eyes.

Their fourteen eyelet height keeps you warm and awakens the inner rebel you always had lurking inside. Everything about the screams Dr. Martens - the yellow threads running alongside the outsoles. The Goodyear welt, keeping the outsole together with the upper, holding on tightly for a long time. The signature padded footbeds, helping you work through their heavy weight with ease. The airWair handy pull tab, easing your way into them. But, surprisingly, a zipper sits on the sides and makes it easy to push your feet in. The rubber soles are chunky, thick and slip resistant, just what a true punk needs.

Amazon Link

6. Rockport Cobb Hill Caroline

Where to buy
Amazon Link
Rockport Cobb Hill Caroline
Amazon Link

The Caroline is a fitting companion for all city dwellers around the globe. The upper comes in leather or suede, in two gentle hues and a vibrant, rusted down red. The stone suede upper also has rustic details, camouflaging them with the rest of your urban companions. Two thick straps crisscross around your ankles, keep you strapped in and give you sharp form.

This upper might seem like your regular run-of-the-mill upper, but it hides a valuable secret - the seams are sealed, waterproofed to perfection, keeping the smallest droplet of water out, making these boots an all-weather shoe! Look your best even in the worst of downpours! Speaking of rain, it can cause quite the trouble in the surface department, making it possible to slip down and injure yourself. This is nothing you should worry about since the rubber outsole and the lead wrapped heel will keep you steady and balanced.

Amazon Link

7. Sam Edelman Petty

Where to buy
Amazon Link
Sam Edelman Petty
Amazon Link

This iconic Sam Edelman bootie finds its way onto our feet and into our hearts time and time again. One of the best things about it is the variety of colors, materials, and patterns it comes in! If you dislike leather, you can always go with suede, and if you feel pain for animals, why not choose the fabric ones? Sleek, clean uppers work great for business surroundings, while the ones with animal prints and glamorous patterns are simply made to be worn to a gala event.

Not all of the models have zippers, and if a zipper is what you’re after, then be mindful when choosing your pair! Their clean design and rounded toes make them super versatile, and allow them to explore every setting with you, be it casual, business or formal. The grosgrain-piped topline gives a western vibe, while also holding the upper together, preventing it from unraveling. The wood inspired outsole offers stability, support, and a stacked, block heel propping you up to new heights!

Amazon Link

8. Cole Haan Harrington

Where to buy
Amazon Link
Cole Haan Harrington
Amazon Link

It’s very obvious here that the zipper was not meant to be hidden! The casual ankle booties sport a chunky zipper colored in brilliant gold, with a lovely tassel detail hanging on the sides, jumping and dancing as you walk. A brilliant attention grab! Their supple upper is suede, a soft and luxurious material that is renowned for its undeniable style. It’s also quite pliable, so you’ll have a cozy experience all around. The slouchy detail contrast the clean upper and gives them drama! Decorative stitching runs along the edges, and a handy pull tab rests on top of the heel counter.

The lining inside is fabric, gently hugging your feet and offering enough air to keep you dry and happy. The leather sock liner is fully padded. This means that you can strut around the whole day wearing the Harrington without fatigue catching up with you! The outsole is what shows us that this ankle bootie is all about comfort - they are lightweight, cushioned with grand Os. technology for the cushiest, coziest touch. You won’t even notice the 35mm stacked heel! The outsole joins the rest of the boot with a welt, so durability is guaranteed.

Amazon Link

9. Fly London Yip

Where to buy
Amazon Link
Fly London Yip
Amazon Link

This chunky ankle bootie just begs to see the light of day, as it will keep you warm and classy without any effort. Every detail here is leather, meant to mold perfectly to the shape of your feet, making it easy to forget you actually have any shoes on. No decorations grace the upper, besides the rouched up waves and a metallic instep zipper on the side.

Simple on the outside, yet secretly frisky - the colorful print on the linings add interesting details once you take the booties off. Now let us mention the obvious - the super chunky rubber wedge! Textured to add style, thick enough to give some serious height, they provide much more support than regular heels do, as they smoothly let you walk as if no heel was present at all!

Amazon Link

10. Naturalizer Jessie

Where to buy
Amazon Link
Naturalizer Jessie
Amazon Link

Naturalizer is a company known for creating comfort footwear, and the Jessie is no exception. Their riding boot silhouette is enhanced by the buckle details - two thin ones wrapped around your calves, and a thick strong one resting on top of your ankles. Their upper is leather, made to keep you warm and cozy. Coming in calm, earthy tones, there won’t be a single clothing combination you won’t be able to work them in.

An elastic gore is sneakily hidden under the buckles, as it stretches to accommodate the strongest of calves. A zipper runs alongside the inner part, making this pair welcoming to all shapes and sizes. There’s a lot of cushioning sitting in the footbed, reinforced with extra heel pads, just so you never have to experience tired and painful feet again. The lining is leather, warm, yet breathable, keeping you sweat free and toasty. It might seem like a stiff boot, but the outsoles provide enough elasticity to keep you on the right path, while the little heel tries its mightiest to give you arch support and balance.

Amazon Link

Sources

  1. Feet Strap Staff, Pros and Cons of Boot Zippers, Listicle
  2. Boot Ratings, www.bootratings.com, The Good and Bad of Zippers!,
  3. Military Boots Superstore Staff, Benefits of Buying a Side Zip Boot, Informational