Best Men’s Ankle Boots

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Are you a man who's been searching for a smart pair of ankle boots? Then you've come to the right place.

Ankle boots are quite popular on the fashion scene at the moment, and quite rightly so with their sleek, smart design, they make the perfect accompaniment to any outfit. We think they're suitable for both casual and formal wear, which is why many men enjoy wearing them.

With so many different styles on the market, we know just how difficult it can sometimes be to find the perfect pair of ankle boots for men. We've done our research and found five of the best pairs of pairs of ankle boots available, which would be fitting for any occasion.

Firstly, we'll discuss the men’s ankle boot in a little more detail to give you an idea of what to look out for before you buy, what they're usually made of, and why you can benefit from by owning a pair.

Fashionable Ankle Boots for Men

Styles of Men's Boots

Since we're focusing on men’s ankle boots in this article, we thought we would begin by highlighting some of the most popular designs for this type of footwear.  

As you shop around for men’s ankle dress boots, you'll begin to notice some similarities between brands in terms of material and design. Mostly, ankle boots are designed using materials such as suede, leather, faux suede, and polyurethane.

Popular styles vary from the sophisticated Chelsea style boot, which is often paired with a good pair of black jeans, to the suede desert boots which include a durable sole with heel and a lace-up design. Other styles include the leather lace-up worker boot, which can be matched up with any style of pants, as well as the biker style boot.

The classic leather style, without laces, is also a popular design when it comes to men’s ankle boots and one which is also famous for work wear. Whichever style of ankle boot you choose, you're bound to look smart, as the specific boot design is sleek and never too casual.

How to Wear Ankle Boots

There are quite a few ways you can style up your ankle boots to look your best.

How to wear Lace Up Boots

If you're looking for a smart appearance with a comfortable fit, then the lace-up style might be for you. Whether you choose to wear them in black or brown, suede or leather, these slick boots look great with a variety of outfits. Lace up boots seem to complement more sophisticated styles. This could be slim-leg trousers, an oxford shirt, and a sweater for a fashionable look.

How to wear Chelsea Boots

Probably the most popular ankle boots worn are men's Chelsea boots. These feature a sleek and minimal appearance and can suit formal as well as more casual outfits. To wear this type of boot for a smart look, perhaps try matching them with a pair of trousers, a shirt, and a long smart jacket. For a more casual look, they can also look good paired with jeans.

How to wear Biker Boots

The biker look is also a trendy one – even if you don’t own a motorcycle. Biker boots usually feature a low heel, buck details and appear to be edgy. Try partnering these boots with a pair of skinny jeans and a neutral t-shirt. To complete the look, a black leather jacket would really set it off! This is an excellent outfit for the weekend or a night out in the city.

What to look out for when purchasing ankle boots?

Before you start even looking for a new pair of ankle boots, you should know what to look out for. You may think that shopping for a pair of ankle boots is simple; however, if you do a little research in advance, you'll be able to purchase the best pair possible. Below see a few considerations to think about before you continue with your shop.

The Weather

Do you live in a location that gets a lot of wet, rainy weather? Then perhaps a suede pair of ankle boots won’t be the best option for you until the season improves. Suede boots can easily be ruined by surface water on the ground, and this means your boots could deteriorate a lot quicker. However, there are solutions to this, which we'll mention in the following point.

Waterproof Protection

If you do live in a rainy area, then a waterproof pair of boots might be best to go for from the beginning, to get the most wear out of them. Leather styles are usually the most waterproof, and so the best option to choose. However, if you do want a suede pair of ankle boots, then you can also purchase a suede leather protector spray, which will protect the boots so that rainwater shouldn't harm them! These sprays can be found from major shoe retailers and are also inexpensive.

Men's Boot Heels

Is height something you like in a boot shoe? If so, then you can also find a good heel on many ankle boots. Some styles will be completely flat, while others can have up to a 2 inch heel. This is also a feature to consider and one which will depend on your individual preference.

Now we'll take a look at five pairs of the best men’s ankle boots.

Comparison Chart

Calvin Klein Men's CHRISTOFF EPI Leather Chelsea Boot, Black, 9 M M US
Steve Madden Men's TACKLED Ankle Boot, Dark Grey, 11 M US
Dockers Men's Stanwell Chelsea Boot, Dark Tan - 9 M US
La Milano Mens Winter Ankle Dress Boots Slip on Monk Strap Buckle Comfortable Chukka Plain Toe Leather Oxford Boots for Men
Calvin Klein Men's CHRISTOFF EPI Leather Chelsea Boot, Black, 9 M M US
Steve Madden Men's TACKLED Ankle Boot, Dark Grey, 11 M US
Dockers Men's Stanwell Chelsea Boot, Dark Tan - 9 M US
La Milano Mens Winter Ankle Dress Boots Slip on Monk Strap Buckle Comfortable Chukka Plain Toe Leather Oxford Boots for Men
Calvin Klein Men's CHRISTOFF EPI Leather Chelsea Boot, Black, 9 M M US
Calvin Klein Men's CHRISTOFF EPI Leather Chelsea Boot, Black, 9 M M US
Steve Madden Men's TACKLED Ankle Boot, Dark Grey, 11 M US
Steve Madden Men's TACKLED Ankle Boot, Dark Grey, 11 M US
Dockers Men's Stanwell Chelsea Boot, Dark Tan - 9 M US
Dockers Men's Stanwell Chelsea Boot, Dark Tan - 9 M US
La Milano Mens Winter Ankle Dress Boots Slip on Monk Strap Buckle Comfortable Chukka Plain Toe Leather Oxford Boots for Men
La Milano Mens Winter Ankle Dress Boots Slip on Monk Strap Buckle Comfortable Chukka Plain Toe Leather Oxford Boots for Men

Last update on 2022-10-01 / Affiliate links / Images from Amazon Product Advertising API

Best Men’s Ankle Boot Reviews

Calvin Klein Christoff Men's Leather Chelsea Boot

Calvin Klein Men's CHRISTOFF EPI Leather Chelsea Boot, Black, 9 M M US

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The first pair of ankle boots featured on our list is the leather Chelsea boots by Calvin Klein. These are a very slick pair of boots that will match with casual and formal styles. We take a look at them in more detail below.


  • 100% leather design
  • Trendy style
  • Synthetic sole
  • Textured leather
  • Versatile boots
  • Durable


  • The boots can scuff as most Chelsea boots do


Calvin Klein is well known for making a fashion statement, and their Chelsea boots are no exception! They've been carefully designed to suit most styles, whether that be a casual look with jeans or a more business office attire pair of trousers.

Real Leather Ankle Boots

When you purchase a new pair of ankle boots, if you're going for the classic Chelsea style, you may prefer to find a leather pair as they're usually the most popular worn men's boot styles. They're great for mixing and matching with several outfit styles and are even waterproof thanks to their original leather design!

Sturdy Fit

Many men also want a pair of ankle boots which will provide support and give them the right amount of sturdiness they need, to stand up straight and look more confident. Some poorly designed boots will lack sturdiness and therefore will not be as comfortable to wear, and possibly cause you to to trip up now and then due to lack of balance.

Two Colors to choose from

Do you want a different color for different outfits? Well, Calvin Klein has thankfully designed their boots in both black and brown leather, so you can either choose one, or both. We think both colors are striking and bound to make a statement!


The best thing about these stylish Chelsea boots is their versatility. They can easily be matched with any outfit of your choosing and will always look good. They're perfect for everyday office wear, as well as any weekends away on vacation or social occasions.


Steve Madden Men’s Tackled Ankle Boot

Steve Madden Men's TACKLED Ankle Boot, Dark Grey, 11 M US

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The next pair of ankle boots featuring on our list is the tackled ankle boots by Steve Madden. These boots are a little different in design in comparison to the previous Chelsea men's boot and instead include a zip up ankle boots design. We take a look at their specifics below.


  • Leather material
  • Synthetic sole
  • Dual functioning zippers
  • Fashionable
  • Comfortable fit
  • Small heel
  • Stitching design
  • Imported


  • These boots had more of a ‘cowboy’ look in person compared to their picture


Steve Madden is a designer from Brooklyn, NY, who creates trendy shoes that are usually ahead of their time. Today, his company continues to produce fashionable, stylish footwear, which continues to be popular with both men and women.   

Comfortable to Wear

When purchasing a pair of ankle boots, you'll certainly want them to be comfortable, and these tackled ankle boots are that! Thanks to their leather material design and a soft synthetic sole, these boots can make walking very easy and at the same time look as stylish as ever. A small heel also allows the wearer to experience increased height, improving confidence levels, while providing a sturdy balance.


These boots feature a zip-up boot style, which gives them an edgier look than the traditional Chelsea style ankle boot. These will match with most of your outfits, whether casual jeans or smart trousers! Mixing and matching these boots will be a lot of fun, and you're sure to make a fashion statement wherever you wear them.

Durable Design

The best feature about these boots is their sustainable design. Thanks to their strong leather composition, they're very sturdy boots and can last a good amount of time. They'll be perfect for everyday wear and also suitable for wet weather.

Two Color Options

If you don’t like the standard black leather boot color, which is often given to the ankle boot, then not to worry as they also come in dark grey and dark tan. This means they're able to match a few different outfits.


Kunsto Men’s Leather Oxford Ankle Boots

The third pair of ankle boots on our list is the Oxford Style boots by Kunsto. These are the first lace up ankle boots we have and are also really stylish. We take a look at them in a little more detail below.


  • 100% genuine leather
  • Soft faux suede lining
  • Stitched cap toe design
  • Wood stacked heel
  • Pull on boots tab
  • Cap toe design
  • Soft insole
  • Fashionable men's boots


  • It's recommended to order a size up with these boots


Are you looking for a pair of lace-up style boots? Well, look no further as Kunsto have the perfect pair for you with their Oxford dress boots for men. These boots feature exceptional craftsmanship and will match most outfits.

Carefully Designed

These boots have been designed using 100% genuine leather material, and feature a hand finished upper, including a pull-on boot tab and a side zipper to slip them on and off easily. They've also been designed with comfort in mind thanks to the soft insole as well as faux suede lining, which makes them so nice to wear. A wood stacked heel also allows for a bit of height when walking, and gives the wearer improved confidence at the same time.

Perfect for Every Occasion

If you're interested in improving your professional office wear, or merely trying a new style of stylish shoe, then these are a great, trendy pair to go with. Thanks to their lace-up design, they give a more formal appearance, instantly smarting up any outfit.

Non-Slip Design

The best feature of these boots is their anti-slip sole. When wearing ankle boots, there's always a fear that they're not the best for cold weather and won’t hold a good grip. These boots, however, are very durable and can be worn even in colder, icy conditions. At the same time, thanks to their soft insoles, they're guaranteed to keep your feet warm.

Three Color Options

The Kunsto men's boots also come in three different colors. This includes medium brown, dark brown and finally, light brown. This gives the wearer a better selection to choose from and the chance to buy a pair in more than one shade to match your favorite outfits!

Dockers Stanwell Men’s Leather Chelsea Boot with NeverWet

Dockers Men's Stanwell Chelsea Boot, Dark Tan - 9 M US

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The ultimate pair of ankle boots on our list is the Stanwell leather slip-on boots by Dockers. These ankle boots offer something a little different to the other footwear on our list and include a very nice NeverWet feature.


  • Artificial leather
  • Durable rubber sole boots
  • Slip on men's boots
  • Three color options
  • Treated with NeverWet water guard
  • Sponge EVA heel pad
  • Comfy foot insole


  • These boots can develop holes in the sole, not too long into ownership. The material also made the shoes less breathable.


Dockers have been making footwear and accessories since 1986 and specialize in making versatile, essential styles. Their Chelsea boots are trendy looking, as well as smart, and are guaranteed to improve any outfit.

Comfort Guaranteed

When wearing boots, it’s nice to wear a comfortable pair. Luckily, these boots have been designed to be very appealing to wear, especially for everyday use. A cushioned sponge EVA heel pad makes sure your heel is nice and cozy, while a fusion footbed features a dual density latex cushion allowing for exceptional, long-lasting comfort.

NeverWet Protection

Unlike the previous shoes on our list, this pair of boots is treated with the fantastic ‘NeverWet’ protection. This is a revolutionary water and stain guard which instantly repels any water or liquids, giving you much better protection from the elements, meaning you can confidently wear them in wet weather. This also protects your shoes from any spillages, keeping them in good condition for longer.


Durability is also vital in an ankle boot, and these Chelsea boots by Dockers can be counted on once again in terms of their longevity. They've been designed with artificial leather, and feature a rubber sole which gives the appearance of authentic crepe. This sole also includes a small heel which will provide some height to the wearer.

Three Trendy Colors

Dockers have designed three different colors of their Chelsea boots, which include dark brown, black and light brown. This gives the wearer more options to choose from, as well as the opportunity to purchase more than one color, to mix and match with any outfit.


La Milano Men’s Ankle Dress Boots

La Milano Mens Winter Ankle Dress Boots Slip on Monk Strap Buckle Comfortable Chukka Plain Toe Leather Oxford Boots for Men

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The last pair of ankle boots for men featured on our list is the Ankle dress boots by La Milano. These boots are certainly very stylish and feature a more formal look. We take a quick look at their specifics below.


  • Slip-on design
  • Stylish tapered toe
  • Versatile
  • Comfort technology
  • Easy to wear
  • Memory foam insole
  • Adjustable buckle
  • Argentinean leather


  • The boots were a little off in terms of sizing


Since 2003, La Milano has made it their mission to create innovative footwear for men, and strive to make the most durable, stylish, and comfortable shoes possible. Their ankle dress boots are high-quality, and are also offered at a reasonable price!

Innovative Comfort Tech+

La Milano prides themselves in comfort tech technology. This means their boots have been designed to be extra comfortable, and you'll get a lot more wear out of them, in comparison to a standard pair. They feature three individual layers which help create a super comfortable shoe. This includes a layer of memory foam, a latex insole, and finally a latex heel cushion.

Timeless Design

La Milano’s ankle boots feature a timeless design. Firstly, they've been designed using premium Argentinian leather with a brushstroke finish. This is such a beautiful material, and gives the shoes a very classic look overall! There is a shiny buckle on the side of each shoe that can be easily adjusted for a better fit, as well as premium style stitching in the boot which finishes their design off nicely.

Perfect for Various Occasions

These boots offer a very sophisticated look, making them ideal for professional work attire, vacation, formal events such as weddings and ceremonies, as well as casual social events. They're versatile enough to be matched up with a variety of outfits.

Easy to Wear

Having boots which are comfortable to wear is also essential. As these boots don’t feature any straps or laces, that makes them quite easy to wear. Their simple slip-on style makes them favorable for everyday use as they can be put on quickly without spending too much time worrying about laces or buckles.


The La Milano ankle boots also feature a very sturdy sole. This is made of a strong rubber composition and is perfect for walking on icy or uneven ground thanks to its anti-slip properties. These boots are therefore great for wearing in the winter months and will keep your feet warm at the same time.


Which are the best men’s ankle boots for me?

To finish, we think that all five pairs of ankle boots for men featured in this article could benefit you by improving your wardrobe, whether for work, vacation or simply strolling in the park!

However, if you're shopping on a budget and would like to buy a pair of boots which are the most reasonably priced, there are some which are perhaps more suited to you. The Kunsto leather Oxford ankle boots, for example, are more inexpensive compared to the Calvin Klein Chelsea boots. This is, of course, down to the brand being so ‘high fashion,’ which of course gives it a higher price tag.

The ankle dress boots by La Milano are also reasonably priced in comparison to some of the other brands, and given that they've been designed with Argentinian leather, they're a pretty good deal!

All of the boots for men on this list, no matter the brand,  should help you spice up your fashion sense. 

And there you have it. Some interesting information on what to look for when purchasing a new pair of boots, as well as some popular styles, and finally how to wear them! We hope this article has inspired you to find some new ankle boot shoes soon, whether for work or casual everyday use.

Last Updated on December 19, 2021 by admin_comfortabledressshoes