There’s absolutely nothing like wearing a cracking pair of Chelsea boots for men to make you feel you can stomp your way through the world. Surely, nothing will dare get in your way. They are a style statement and ego boost in one. Now, Chelsea boots for men are becoming extremely popular.

You know about Chelsea boots, we’re sure. You know, those ankle-high pull-on boots that come with stretchy elastic material on ankles. Ah, now you remember!

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Mainly, these are ankle-length boots with rounded toes, low heels, and two parts (the quarters and the vamp), made using a single piece of leather. There are no fancy buckles, laces or anything else either. Rather, it’s “put on and go” with Chelsea boots for men.

That is one of the biggest draws to these boots too.

Best Chelsea Boots for Men

1) Giorgio Brutini Chelsea Boot

Brand Name
Giorgio Brutini
3 Pounds
Main Material

This pair of ankle-high Chelsea boots is an attention-getter and looks great with most of your outfits. The streamlined design coupled with full leather construction gives it an upscale look.

Keep in mind that the lower back portion of these boots is actually made of a synthetic material, but that actually adds to its design and help you wear them with slacks, jeans, etc., which is great.

The insole padding really helps keep you comfortable when wearing the boots. The use of rubber soles and heels means the boots stay comfortable irrespective of where you wear them.

With a boot opening of 12.5”, it provides a nice fit. The presence of elastic gores and pull-on loop at heel means that you will find it easy it slip it on. While the fit looks reasonably good, some people have complained about the size being not true to their original foot size.

They believe ordering a size up is a good idea, but we think that is mainly for people with wider feet.

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  • It is made of high quality leather for durability.
  • It uses a synthetic sole that is quite comfortable.
  • It has a pull-on loop at the heel to make it easy to wear.
  • You may have to order a size up for a perfect fit.


2) Steve Madden Highline Chelsea Boot

Brand Name
Steve Madden
3 Pounds
Main Material

If you’re looking for good quality suede Chelsea boots, these boots from Steve Madden will not disappoint. The combination of suede upper and crepe sole means that you will feel comfortable wearing the boots and they are going to serve you nicely for years to come.

The fresh pull-on style is quite unique and comfortable too. It adds a degree of versatility to these Chelsea boots. The good thing is that they are true to your original size and there is hardly any chance to order a size up or down. Just stick with your original size and they are likely to fit in just fine.

We really like the quality of the elastic sides, which is loose enough to help you slip it on and off, but tight enough to keep your foot locked in place. These boots are quite impressive as a whole, but keep in mind that quite like other suede boots they cannot resist the rain very well.

Fortunately, they can do just okay if you, mistakenly, step in a puddle.

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  • It uses the suede upper for added durability and style.
  • The boots come with a crepe sole to keep you comfortable.
  • The boots fit in right so no need to order a size up or down.
  • You will not find it do very well in the rain.


3) Dr. Martens Oakford Chelsea Boot

Brand Name
Dr. Martens
4 Pounds
Main Material
Grizzly Leather

With its synthetic sole but genuine leather upper, the Oakford Chelsea boots are going to impress you for sure. The first thing you notice when you wear these boots is that they super comfortable. The credit goes to its air-cushioned, synthetic sole that is somewhat soft but quite durable because it is double-stitched to the upper.

The soft leather – grizzly leather to be precise – is also going to add to the grace and quality of the boots. The Goodyear-welt construction means they are going to last for a long time. The slip-on design means you will not have to face any issue wearing them quickly.

The design looks cool with subtle rib detailing. However, it is important to mention that the heel height may not suit some people. It takes some getting used to the height to feel more comfortable walking around in these boots.

Nevertheless, these slip-resistant boots look good and perform great in all kinds of weather.

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  • The upper uses grizzly leather that keeps you comfortable.
  • Double-stitched sole for added durability.
  • It has a fat and oil resistant outsole for added traction.
  • The heel height is 1.25” that may not work for everyone.


4) Duke Chelsea Boot

Brand Name
Thursday Boot Company
3.5 Pounds
Main Material
Tier 1 Full Leather

The men’s Duke is a popular Chelsea-style boot known for its durability and versatility. You are not going to find issues in terms of durability because the use of Tier1 full leather upper means that it can withstand the elements quite effectively.

The sole is of high quality as well, but the good thing is that the boot can be resoled easily. With its Goodyear welt construction, it offers a good value for money.  It means that if you take good care of these boots, they will stay with you for a very long time.

It uses a low-profile studded rubber outsole that means that the boot will maintain stability in any setting. The only issue is that the boot may be perfect lengthwise but may not fit perfectly when you have slightly wider than normal feet.

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  • The use of Goodyear welt construction for added durability.
  • It comes with glove leather lining for comfort and style.
  • It offers good traction because of a low-profile studded rubber outsole.
  • The size may not work for some with wider feet.


5) Crevo Denham Chelsea Boot

Brand Name
8 Ounces
Main Material

These stylish Denham boots are quite suitable for men looking for classic Chelsea boots. Though it uses a synthetic sole, the upper is the real selling point for this pair. The quality of the leather used is quite impressive and seems to have the potential to withstand the elements.

It is easy to wear these boots, thanks to its classic double-gore silhouette and highly functional back pull-tab. It is equally comfortable to walk around in these boots because they come equipped with a memory foam sock for serious comfort.

The styling is nice, especially when you opt for the brown leather that seems to have a fine textured print. The sizing is reasonably good, but you should remember that the boot opening is 10.25” around, so pick a size accordingly.

Overall, it is nice, but the price may be a bit on the higher side.

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  • It features goring side panels for an ease of wearing.
  • It comes equipped with a non-slip outsole for added traction.
  • It uses a memory foam sock for added comfort.
  • Could do with a little more padding.


6) Steve Madden Simon Chelsea Boot

Brand Name
Steve Madden
1 Pound
Main Material
Leather and synthetic

The combination of leather and synthetic seems to work just fine for this Chelsea boot from Steve Madden. The upper uses genuine leather, so it is going to become more comfortable as you break in the boot. The use of smooth surfaces and elastic goring means that you can expect an easy and convenient pull-on entry.

The shaft has a 5.5” length from the arch, which is quite standard, but it is important to notice that there have been some complained about the boots not being very true to the size. moreover, the heel height, at 1.25”, may not work for everyone.

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  • It has a quality leather upper for a luxurious look.
  • It is quite true to the size.
  • It comes equipped with a rubber sole for better stability.
  • Its heel height may not suit every wearer.


7) Dockers Ashford Chelsea Boot

Brand Name
1.25 Pounds
Main Material
Full-Grain Leather

The finest Chelsea boots use full grain leather, and that is exactly what you get when you opt for the Ashford Chelsea boot from Dockers. The use of genuine leather makes it a preferred choice for those who value quality over price. Many customers have confirmed that the leather is of the highest quality and wears well.

The best thing about full-grain leather is that it looks better with age, and that makes the Ashford Chelsea boot a popular choice.

You’re less likely to experience any sizing issue with this pair, but keep in mind that shaft measures around 6 inches from the arch. The rubber sole looks solid and is likely to handle regular use with ease. To make it comfortable, the company has used the Comfort Zone Technology.

This means you can see a cushioned EVA heel pad, a latex footbed, and Fusion Footbed. These three zones of comfort ensure that you stay comfortable no matter often you wear the boots.

It is worth mentioning that the styling of the boot may be a hit or miss because some people just love the plain, classic look, whereas the Ashford Chelsea boot has brogue accents and handcrafted details. If you’re a fan of such details, the boot is going to impress you for sure.

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  • It comes with a rubber sole for good durability.
  • It uses Comfort Zone Technology for impressive cushioning.
  • It has an upper made from full-grain leather.
  • The brogue accents and details may or may not work for everyone.
  • The price may be a bit high.


8) Metrocharm MC137 Ankle Boot

Brand Name
2 pounds
Main Material

Available in classic black and brown colors, the MC137 by Metrocharm seems to be a good Chelsea boot to wear with your formal outfits. It sports a unique spherical toe design that adds to its style. With the height of the platform around 0.25”, it works quite well for formal as well as party wear.

Thanks to the presence of a cushioned footbed insole, you will not feel uncomfortable wearing these boots.  Speaking of comfort, it is important to order the right size, which is easy considering the boot is quite true to the size. You can order as per your foot size and it should work fine.

The non-skid outsole is also a good addition. While the boot is quite comfortable, you may find it to be a bit on the expensive side as compared to other boots in the same category.

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  • It is a lightweight yet stylish Chelsea-style boot.
  • It works great for all occasions and outfits.
  • It comes with a non-skid outsole for better stability.
  • It may feel a bit expensive than other similar boots.


9) Bruno Marc Chelsea Ankle Boots

Brand Name
Bruno Marc New York
3 pounds
Main Material
Faux Leather

To pull off a comfortable yet stylish look, you can place your trust in these casual Chelsea boots. While it uses faux leather upper, it looks good with its fur lining. The slip-on design, which is the trademark of Chelsea boots, works amazingly well, and the elastic side panel simplifies the task of wearing the boots quickly.

To enhance the comfort, the company uses a cushioned footbed. The midsole is reasonably good, and so is the non-skid outsole that offers good traction in all settings.

Another good thing is that the sizing is quite perfect and the boots do not run narrow like Chelsea boos for men might from many other brands. The round-toe design means that you are likely to feel comfortable in these boots even if your feet are slightly wider.

Due to the faux leather, they hold up nicely even when if it rains. Just remember that faux leather may not be as desirable as genuine leather that tends to age very well.

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  • It uses faux leather upper for comfort and style.
  • It has a round-toe design and an elastic side panel for the ease of wearing.
  • It is true to the size and works great for people with wide feet.
  • It uses faux leather that may not be as durable or desirable as genuine leather.


10) Timberland Carter Notch Chelsea Boot

Brand Name
5 Pounds
Main Material
Ful-grain Leather

These business casual boots work great with most of your outfits, and you can even wear them with your jeans or khakis without alerting the fashion police.

The use of a high-quality leather upper means you will find it comfortable and it will last a long time as well. In fact, the company claims that the upper uses premium waterproof leather. Though many customers believe it is not as waterproof as the company claims, it certainly performs much better than other Chelsea boots in this regard.

Something that you will appreciate about these boots is the comfort they offer. The use of leather upper is one reason, but the presence of anti-fatigue, fully removable footbed makes it even more comfortable to wear. The pull-on style coupled with dual stretch gore means it is easy to wear these boots.

Overall, the boots are great, but you may find the pair to be a bit expensive.

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  • It uses full-grain waterproof leather.
  • It comes equipped with an anti-fatigue footbed.
  • It is great for a business look and goes well with jeans and slacks.
  • The price may be a bit on the higher side.


11) Dr. Scholl’s Shoes Credence Chelsea Boot

Brand Name
Dr. Scholl’s Shoes
1.12 Pounds
Main Material

This is a rugged Chelsea boot that is going to last a long time. It uses suede upper, which certainly requires some upkeep but is capable of serving you well for years. The good thing is that even though it looks rugged and rather masculine, it still looks modern because of its clean silhouette and sleek design.

The shaft measurement is about 5.5 inches from the arch and the sizing is close to perfect. Just order the size you usually wear and you will not find any issue in terms of fit. Its memory foam insole is also comfortable and keeps your food secure inside the boot.

The crepe-lie rubber sole is responsible for making these Chelsea boots for men one of the most comfortable shoes around. If you know what it takes to care for suede, you may certainly want to order this pair.

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  • It uses suede for added durability.
  • It comes with a memory foam insole for maximum comfort.
  • It uses laid on stitch welting to help it maintain its presence.
  • The suede requires serious maintenance and care.


12) Clarks Bushacre Up Chelsea Boot

Brand Name
1.2 Pounds
Main Material
Beeswax Leather

Made of beeswax leather, the Bushacre up Chelsea boots from Clarks look quite impressive and professional. They serve as a perfect choice to match your business attire. The use of this premium quality leather also promotes breathability and keeps your feet dry.

These stylish yet rugged boots can resist water very well, which is an added benefit.

The rubber sole keeps things comfortable, but some people are of the view that the sole does nothing to improve the amount of traction. However, you’re going to see similar types of soles on all boots from Clarks, so you will have to bear with this actually.

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  • It used beeswax leather for improved breathability.
  • The outsole is made of rubber that helps absorb shock.
  • It has Ortholite footbed to provide you with maximum comfort.
  • The outsole may not offer great traction.


13) Calvin Klein Larry Calf Suede Ankle Boots

Brand Name
Calvin Klein
1.25 Pounds
Main Material

For all those suede lovers looking for a perfect Chelsea boot to include in their collection, this pair from Calvin Klein is sure to serve the purpose well. With high-quality suede upper, the boots are extremely comfortable. There is also some use of leather in detailing that makes them a good choice to wear with your jeans and casual outfits.

In terms of sizing, you will find mixed reviews. Most people believe that these boots run narrow, and that is actually true. You may be better off ordering half a size up than you normally do to get a perfect fit. That is especially true if your feet are a little too wide.

The boots are extremely comfortable and warm, but you may have to be a bit careful when wearing in rainy conditions. You may want to have some leather boots as your primary winter boots because the bootie from Calvin Klein has its limitations.

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  • It uses suede to keep you warm and comfortable.
  • It comes with a sturdy rubber sole for durability.
  • It is available in different colors to suit your needs.
  • The sizing may be an issue as the bootie runs narrow on the feet.


14) Steve Madden Saine Chelsea Boot

Brand Name
Steve Madden
14.6 Ounces
Main Material

When looking for the finest Chelsea boots, you can certainly pick something from the Steve Madden collection, and this Saine Chelsea boot will not disappoint in terms of quality. It uses leather upper, so you can expect it to be comfortable and age well over time.

The shaft measurement is 5 inches from the arch, whereas the platform is around 0.5 inches. Because of the leather, you may find it a bit tight when new but the leather will become loose after you’ve have broken in the boot.  The sizing is usually not an issue, but some people have complained about the boot running a bit large.

In most cases, however, you will be just fine ordering your usual size.

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  • It uses important leather for a premium look.
  • It has a rubber sole to withstand the rigorous use.
  • It has a modern look and works well with jeans and suits.
  • It may be a bit expensive.
  • The sizing may cause some issues for some people.


Ready for a bit of boot history 101?

The Chelsea boot was first introduced to the world by one J. Sparks-Hall who had the prestigious job of bootmaker to Queen Victoria herself. It’s impressive that it’s still going strong. There must be a reason for all this success if you ask us.

While we all know the Queen obviously knew her boots, her style was not really insane compared to some we might see today. Her boots were plain and unadorned, but do keep in mind that this was the style of her time.

These days, they come with all sorts of extras. Think stuff like brogues, medallions, and fancy cap toe detailing. Queen Victoria might not have been amused but such things are the style of our time. Many men find them impressive looking, as they help them make a perfect style statement for them.

Which Clothes Do Chelsea Boots For Men Go With?

The short answer is everything, with very few exceptions maybe. They are extremely versatile which is what makes them a wardrobe must. Wear Chelsea boots for men with jeans or a suit and no one will bat an eye.

The clean and simple lines complement any outfit and leading designers are forever matching them into the latest fashion wear-  useful to know if you know the fashion trends and follow that sort of thing.

Just to make sure your booty style statements rocks, there are different styles you can check out. Thick chunky soles create a casual look that means business. The new slimmer sole is perfect for the more formal occasion. A higher ankle is the vogue at the moment but it’s all up to you really.

These boots have their own style rules so experimenting, chopping and changing to suit what you are wearing, where you’re going and how you feel, just add to your boot wearing versatility. Slim jeans coupled with a crisp white shirt and a smart wool coat is one way forward but with so many style possibilities, it is a case of check it and see.

However, generally speaking, avoid the chinos. Not the best way to show off your Chelsea boots for men, at all.

Consider the Colors:

Chelsea boots for men are now available in different colors. So, when you believe it’s time for a new outfit and boots to match, you have to consider boot color too for the perfect look. It’s a bit of fun old Queenie didn’t get to indulge in. Just by experimenting with colors, you can create a completely different style statement.

Here are a few suggestions for your consideration.

A pair of burgundy Chelsea boots is an all-around option. Good with everything.  Similarly, if you want to stand out and be noticed for the fashion icon you are, choose from the more exotic colors, such as green, blue, red, or even yellow.

Boots with Suits:

If you think only brogues, Oxfords, or loafers are suiting suitable footwear, you’re missing out. A correctly selected pair of Chelsea boots can work wonders to sharpen your business look. It is easy to carry off brown leather Chelsea boots for men with a stylish grey suit and create a smart look effortlessly.

Try matching the dark brown Chelsea boot with the classic navy or dark blue business suit and let the bottom of your trousers sit over your boots. It’s a classy combination for a classy business look and a contrast that works surprisingly well.

Some points to consider when you want to be suited and booted;

Chelsea Boots with Jeans:

Chelsea boots work as efficiently with a pair of jeans as they do with your favorite classic suit. It is the uber-stylish classy look. Make it even better by pairing with a casual jacket and a stylish t-shirt underneath.

Who wouldn’t want to wear their Chelsea boots with jeans? It’s as natural as ham and eggs. Even so, to keep things bootily perfect take into account the material the boots are made from as much as the color. These details matter when you are a style leader after all.

Matte or suede creates a laid-back look for when you are taking things easy. But for casual smart, patent leather and high shine are just the ticket to get you noticed. A pair of black suede Chelsea boots will go with most jeans colors and styles and versatile enough to be worth the cash spent any time.

This is especially true if you are getting your wardrobe together on a budget.

Choose correctly to bring out your cool rockstar look by pairing with a leather jacket. Your Chelsea boots with jeans will create a modern refined look. Like Kanye West, keep things refined, by opting for a pastel color palette. Combine grey jeans with a plain shirt, a biker jacket, and black Chelsea boots to complete your smart look.

Some Rules to Consider to Keep You Looking Sharp:

Are Chelsea Boots For Men Comfortable?

You all know that Chelsea boots are stylish, but because of their rather bulky appearance, some men often ask about how comfortable these boots really are. Apart from the fact they have stood the test of time, the comfort depends on the fit, material, and probably the shape of your foot.

Sizing Matters:

It is a good idea to buy a pair of Chelsea boots if you’re looking for boots that fit snugly and sit nicely to your foot and ankle. To ensure that the boots are comfortable, you need to be careful about the sizing. Pick the right size only. There’s no ‘it’ll do’ here just because you’re shopping and would rather not be.

It’s important to get the fit right around your ankle as much as it to get the right length. A loose boot will be uncomfortable and for the sake of a bit of shopping perseverance, you’ll have wasted your cash.

And here’s why a good fit is so important. The Chelsea boot is not like regular footwear. This close fitting boot has its flexibility in the side panel. Traditional shoes have flexibility in the instep. The good thing is that Chelsea boots for men enjoy a reputation of being true to your actual foot size.

This is obviously helpful!

However, you still need to try them on and walk about a bit to get used to the side panel fit and make absolutely sure they are good to go. Here, you should consider if you’re going to usually wear the boots with thick socks because that would mean buying a pair with half a size bigger than your foot size.

Elasticized Panel:

Chelsea boots are comfortable because they have an elasticized panel to keep your foot secure. There will be a handy tab or loop at the back of your boot that you can use to pull them on with ease. Chelsea boots may feel a bit tight in the beginning because of their slightly narrow construction.

Thankfully, they tend to stretch out once you have broken them in nicely. Depending on the material used, the foot bed usually molds decently to your foot, making them even more comfortable over time.

The Price and Comfort:

Most Chelsea boots are made of leather, and are going to feel comfortable only when the leather is of the highest quality. When you know you get what you pay for and high quality leather comes at a high price, don’t expect those under $100 boots to compete with $500 shoes in terms of comfort.

When you opt for cheaper Chelsea boots, you get the upper glued to the sole not stitched. The quality of leather used may not be that impressive either. Boots made of cheap calf leather will eventually leave you dealing with some nasty creases.

Construction Method:

It is sensible to give some thought to the construction method of any Chelsea boots you have your eye on to determine the quality. With a stitched construction, that can be resoled and used for many years, you get excellent value for money. For leather, opt for shoes made of full grain leather for comfort and durability.

Full grain leathers tend to age better compared to corrected grain leather that usually comes with a plastic coating. High quality fine-grained calf will always prove to be the most comfortable option but be prepared, they are expensive.

Sole Quality:

The quality of the sole matters, a lot. You can get rubber soles that are comfortable, but there are other options, such as vibram, lugged, or crepe that are casual yet more comfortable. A leather sole is a nice choice too, but you will have to protect it by using a thin sole protector.

What Materials are Chelsea Boots For Men Usually Made Of?

Chelsea boots are now available in different materials, but the traditional ones have always used variations of leather. Today, it is possible to find them in suede too.

Going for Suede:

Suede Chelsea boots look great and are quite durable too, but you have to consider where and when you will be wearing your boots to decide if they are going to work for you or not. While suede exudes a sense of luxury, it demands a lot more upkeep.

If you’re in an area where it rains a lot or you have to deal with muddy walking conditions, you will be wasting money on suede boots because they cannot withstand moisture. They are the best for dirt-free environments.

Going for Leather:

For the classic look, you can always put your money on real leather Chelsea boots. They are perfect to create a sophisticated look, but pair them with jeans and the look goes rockstar supersonic. They are low-maintenance boots and age amazingly well.

They also work great for winter and autumn use. Opt for the ones that come with repairable soles and elasticized gussets and they will serve you well for years.

Caring for Your Chelsea Boots:

Leather boots look great but you need to take the right care of them ensure they keep looking perfect. To keep them clean, simply take warm soapy water and soak a cloth in it. Remove the excess water and use it to clean your leather Chelsea boots for men.

Work in a soft rotating motion to get rid of any dirt marks. Finally, apply brown or black polish to give your boots a new look.  Try using a soft bristle brush here to buff the polish into the leather.

To take the right care of your suede Chelsea boots, you may consider buying a suede protective spray. The spray will offer some protection against the elements. Be sure to clean your boots before applying the spray. You may also want to invest in a suede brush to help maintain the nap or the surface of the suede.


The fact of the matter is Chelsea boots are popular because of their simplistic yet highly attractive classic look. Made using high-quality leather, they give you a timeless charm. It wouldn’t be wrong to suggest that when paired with the right clothes, they give you an old-fashioned alpha male power.

Just select the right color to go with what you’re wearing and pay special attention to sizing before finalizing your buying decision.