7 Best Men’s Chelsea Boots to Wear With Everything

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best chelsea boots

There’s plenty of great shoes out there, but sometimes you just need something a little more out there.

If that’s what you’re after, Chelsea boots are for you: after nearly 6 decades, they still look as Rock and Roll as ever.

The best Chelsea boots don’t only look cool – they’re comfortable and durable.

It’s just that most men struggle to find the right Chelsea boots for them.

So we’ve put together this review with the 7 very best products on the market.

In a hurry? Here are our top picks:
Blundstone Original 500 Series

Our no.1 choice – the Blundstone Original 500 Series – are an ultra-comfortable boot made from super sturdy leather. They truly are the most comfortable Chelsea boots you’ll find.

Thursday Boot Company’s Duke Chelsea Boots

Our no.2 choice are Thursday Boot Company’s Duke Chelsea Boots, which are beautifully handcrafted with a great, stylish design.

And that’s not even it:

We’re also going to give you a detailed guide to proper Chelsea boot care and help you understand the difference between Chelsea boots and Chukka boots.

First, let’s look at 7 things you need to think about when choosing your Chelsea boots.

Quick summary

bb2-table__imageBlundstone Original 500 Series
  • Ultra comfort
  • Made with strong, sturdy leather
  • Reduces tension on your feet
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bb2-table__imageThursday Boot Company Duke Men’s Chelsea Boot
  • Beautifully hand crafted
  • Looks good
  • Offers comfort all day long
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bb2-table__imageBruno Marc Men's Suede Leather Chelsea Ankle Boots
  • Very affordable
  • Slip-on design
  • High quality suede leather
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bb2-table__imageSkechers Men’s Segment-Dorton Chelsea Boot
  • Super durable
  • Lightweight and comfortable to wear
  • Plenty of breathing space for your feet
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bb2-table__imageParty Men's Casual Chelsea Boots
  • Affordable
  • Lightweight and comfortable
  • Excellent for casual wear
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bb2-table__imageDr. Martens 2976 Chelsea Boot, Black Smooth 
  • Slip-proof
  • Sturdy for workwear but still comfortable
  • Memory foam cushioning
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bb2-table__imageCrevo Men’s Denham Chelsea Boot
  • A look that catches the eye
  • Affordable option
  • Offers plenty of traction
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Before you buy: 7 Things to consider when purchasing Chelsea boots

Before spending your hard-earned money on a pair of quality Chelsea boots, it’s important to keep a few things in mind to ensure you’re making the best choice.

1. The fit is everything

A Chelsea boot is close-fitting and will have more flexibility in the side panel than in the instep. You want to find a boot that fits snugly but isn’t too tight, so finding the correct size is everything. The last thing you want is for your feet to feel sore and pinched.

While it’s always important to have your feet measured before buying any footwear, it’s as important to try on your Chelsea boots rather than relying on a standard shoe size chart entirely.

The bottom line is that you’re looking for a snug fit that’s not too tight.

2. What’s the material?

You’ll have a choice of suede or leather regarding Chelsea boots. Suede has a more “luxurious” look but requires more upkeep – especially in wet and muddy weather conditions.

That said, dry and dirt-free environments are best for suede-wearers, unless you don’t mind regular maintenance, or don’t mind taking the risk of ruining your boot.

Leather is fine for autumn and winter – and, really, any weather condition – but make sure you invest in boots with high-quality repairable soles no matter what material makes up the upper.

3. Chelsea boots have sole

Well, all footwear includes a sole, but your best bet with Chelsea boots is a leather sole. While many boot manufacturers use a variety of materials to make soles, leather represents the traditional, classic look.

4. Elastic or zipper

You’ll find Chelsea boots that fasten with a zipper rather than the traditional elastic. But, just so you know, “true” Chelsea boots fasten with elastic, not with a zipper. That quality of the elastic

fastening is very important not only for comfort but also for the shape and longevity of the boot. Plus, a swanky-looking elastic gusset looks great with trousers that are slightly shorter than normal.

5. The color

Black is the traditional color of Chelsea boots and probably a good choice if you’re buying your first pair. Then again, it’s a free world: choose whatever color you’d like.

6. Keep it simple, or maybe not

Chelsea boots come in a variety of styles that keep up with today’s fashion trends – whether it’s pointy toes, high-shine patent leather, or colored soles. You shouldn’t have a hard time finding a pair that fits your fashion sense.

Keep in mind, however, that traditional black or brown Chelsea boots never go out of style and work well with whatever you’re wearing.

7. But a quick word about color

While you should have no trouble finding a Chelsea boot in your favorite color, choose wisely. For instance, brown suede is great for a country look, while black represents a more urban look.

Burgundy, meanwhile, is a good all-around option, while exotic colors like blue, red, yellow, and green are ideal if you want to make a personal fashion statement.

Just a quick note regarding color: black Chelsea boots look best with dark suits, while brown boots pair best with suits of medium and lighter colors. Burgundy is very versatile and works well with almost every other color.

Now that we’ve covered a few handy buying suggestions, it’s time to move on to the best Chelsea boots for men.

The 7 best men’s Chelsea boots

1. Blundstone Original 500 Series

Blundstone Original 500 Series

Affectionately known as “Blunnies” in Australia – where the Blundstone company has its headquarters – the Blundstone Original 500 Series is an iconic brand with a strong reputation.

There’s a lot to love about the BL500 Series, not the least of which is classy styling and craftsmanship that has everything you want in a casual work boot. It’s also very comfortable and should last you a good long time.

Let’s take a closer look:

  • Blundstone’s Original 500 series features a shock protection system that reduces the impact on your soles by 33 percent.
  • It comes with a removable footbed that wicks moisture away to add further comfort and dependability.
  • The polyurethane outsole is dual-density and injection-molded to make for a softer step.
  • It comes with elastic side panels that make it easy to take the boots on and off.
  • The heel pad features XRD Technology that provides even further shock absorption.
  • The midsole also features polyurethane construction to provide support and comfort.
  • The boot also has an ergonomically-designed toe bed that helps reduce foot fatigue.
  • The sole is slip-resistant.
  • The lining includes soft leather.

Some other features we like about the Blundstone 500 include finger loops that help make taking the boots on and off that much easier. Finally, Blunnies come in a variety of colors – just choose the color that best fits your clothing.


  • Very comfortable
  • Sturdy, leather construction
  • Reduces stress on your feet


  • Be careful about sizing<

Bottom Line

Blundstone goes the extra mile in creating comfortable boots that look and feel good. The 500 Series is ideal for casual work wear, sturdy, and designed to last a long time.

2. Thursday Boot Company Duke Men’s Chelsea Boot

Thursday Boot Company Duke Men's Chelsea Boot

Ah, the rich honey suede. The classic Chelsea design. Yes, there’s plenty to like about Thursday Boot Company’s Duke Men’s Boot.

You even have to like their determination to put the best possible product on the market.

The folks at Thursday Boot Company made 20 re-designs of their Duke’s Men’s boot before settling on a final product, which happens to be the best suede Chelsea boots and certainly among the best Chelsea boots for men.

Here’s a look at some of the Duke Men’s Chelsea Boot’s features:

  • The honey suede upper is distinctive and helps make the Duke a boot you can wear for most occasions – formal or informal.
  • The elastic on the outsole is firm enough to keep your ankle locked into position without abrasion. These boots will stay snug no matter what the activity.
  • The Duke even comes with Goodyear welt construction that provides added support and durability.
  • Thursday Boot Company uses a blended solution of waterproof and hydrophobic construction that’s applied to leather at the beginning of the tanning process. Doing so helps water from penetrating the leather.
  • The insole consists of an EVA comfort strip on that’s attached on top of a cushy cork midsole – all of which resides under a leather lining. The Duke forms to your foot to provide all-day comfort, which is quite a plus if you’re on your feet a lot.
  • Thursday Boot Company makes all of its shoes and boots in small batches and places a premium on quality construction.
  • The heel is firm and durable, while the toebox has a round, rakish look.
  • You’ll love the feel of the Duke’s suede: it’s soft and pliable and fights creases with an elasticity that’s uncommon for a boot’s upper. And it simply looks good.
  • Last but not least, the Thursday Boot Company treats all of its boots with a WeatherSafe treatment that protects against inclement weather.


  • Excellent craftsmanship
  • Looks great
  • Provides all-day comfort


  • Make sure you size it carefully because you’ll probably need to choose one size smaller than normal

Bottom Line

There are plenty of excellent suede Chelsea boots on the market, but for our money, the Duke is your best choice. Comfort, style, durability – it has it all.

3. Bruno Marc Men’s Suede Leather Chelsea Ankle Boots

Bruno Marc Men's Suede Leather Chelsea Ankle Boots

Every pair of boots we’ve discussed on this list is great, but let’s be real: most of them are pretty darn expensive. So if you’re looking for something that can compete on quality but won’t burden your wallet so much, Bruno Marc’s Suede Leather Chelsea Ankle Boots are the one.

They’re made of premium suede leather and come in a great variety of colors – giving you plenty of choices.

While the material lacks breathability – leading some reviewers to feel they’re a little too much to wear for long stretches – there’s plenty of extra comfort features that should keep most happy.

The slip-on design also ensures that they’re more casual than most Chelsea boots, and with their cushioned footbed and smooth fabric lining, they’re surprisingly comfortable.

The material is huge durable, and most seem to find the fit very comfortable – though some complain that they are a little narrow.

Ultimately though, the quality of the construction and leather is exceptional for this price – anyone looking for a great deal should look no further!


  • Great price for the quality
  • Premium suede leather
  • Slip-on design


  • Lacks breathability

Bottom Line

High quality and affordable: a great boot for men who love a good deal.

4. Skechers Men’s Segment-Dorton Chelsea Boot

Skechers USA Men's Segment-Dorton Chelsea Boot

The diverse Skechers line continues to grow, as does the company’s popularity worldwide, thanks to its wide range of quality products. Their Segment-Dorton Chelsea Boot is a prime example of both their diversity and high quality and belongs in any Chelsea boots review.

There are a lot of things we think you’ll like about the Segment-Dorton Chelsea Boot, including their superior comfort.

Of course, comfort is always vital when choosing a Chelsea boot; the Segment-Dorton is excellent for walking because of its lightweight nature.

You’re assured of excellent comfort even if you spend long portions of your day on your feet and moving around.

The insole adds a layer of comfort that contributes to the Segment-Dorton’s comfortability, and, like the outer sole, it’s extremely durable.

The insole is gel-infused with memory foam that adapts to your foot’s unique shape and your stride. The boot’s ankle-high length also contributes to its overall comfort.

Here’s something else to like: the Segment-Dorton offers plenty of roominess – not so roomy that you don’t get a snug fit, mind you – but roomy enough that you can wear thicker socks without pinching your foot.

The Segment-Dorton features an oil-leather upper (the leather comes from China) as well as goring side panels and a rear pull loop for easy on-and-off function. Ignore the “Made in China” myths because the leather is of the highest quality.

It’s worth mentioning the Segment-Dorton’s durability again because they’re among the most durable Chelsea boots that you’ll find anywhere. Whether you’re wearing them to work, or walking on rugged terrain, these boots will hold up to the stress and strain.

Moreover, the boots are waterproof, although you don’t want to expose them to constant moisture.


  • Superior durability
  • Lightweight and comfortable
  • Roomy


  • They may run slightly wide

Bottom Line

Segment-Dorton is a good all-around Chelsea boot that’s great for casual wear but also suitable for the workplace, especially if you spend most of the workday on your feet. They’re also affordable and a great bargain for the price.

5. Party Men’s Casual Chelsea Boots

Party Men's Casual Chelsea Boots

A higher price doesn’t always signify higher quality. Case in point: Party’s Casual Chelsea Boots, which won’t break the bank but won’t let you down with cheap craftsmanship, either.

“Casual” is the right word, as well, because these brown boots are ideal for casual and smart casual occasions and pair well with chinos and jeans. That’s not to say you can’t wear them with dress pants but, again, they’re best-suited for casual wear.

They’re also exceptionally comfortable, and you can walk around in them all day without experiencing foot fatigue or soreness. And they’re lightweight with nice leather construction and, for the price, very durable.


  • Lightweight construction
  • Affordable
  • Great for casual wear


  • Fit may be a bit snug

Bottom Line

At this price, you can buy a second pair of the Party Casual Chelsea Boots and not worry about wearing them out too soon. They look great and are very comfortable.

6. Dr. Martens 2976 Chelsea Boot, Black Smooth

Dr. Martens 2976 Chelsea Boot,Black Smooth

Few companies have quite an iconic history as Dr. Martens. It began with Dr. Klaus Maertens injuring his foot in a skiing accident in the Bavarian Alps. To aid his recovery, Dr. Maertens designed a shoe with an air-cushioned sole that relied heavily on old rubber tires.

The rest, as they say, is history.

The Dr. Martens company – renamed to sell its shoes and boots in England better – has come a long way since then, and like the Chelsea boot, in general, became a symbol of a free-spirited attitude (some would say “rebellious”) and self-expression in the 1960s.

The brand endures today and offers something for people of every class and culture.

Including, that is, their 2976 Chelsea Boot.

The 2976 is comfortable and sturdy and has a rugged sole that makes it ideal for workwear. It comes with a leather and textile (synthetic) upper, woven stretch goring inserts, and the Dr. Martens logoed pull-on top above the heel.

It also has a removable insole to go with a SoftWair comfort footbed that includes memory foam cushioning.

While the 2976 has a leather upper, the Dr. Martens brand gets props for producing four styles of footwear that are 100% vegan. Rest assured, the company builds those styles with solid construction and with the kind of traction that makes them slip-resistant.

Moreover, their styles – including the 2976 – are handmade. Beating their craftsmanship is tough. You can always pair them with a nice pair of jeans.


  • Slip-resistant
  • Comfortable but sturdy enough to serve as workwear
  • Memory foam cushioning


  • It takes a little while to break them in

Bottom Line

The Dr. Martens brand is well-known and favored by many people worldwide. The 2976 is one of the best in its quality line of boots and is a great choice for anyone looking to give Chelsea boots a try.

7. Crevo Men’s Denham Chelsea Boot

Crevo Men's Denham Chelsea Boot

The Crevo Men’s Denham is another Chelsea boot that’s suitable for professional and semi-formal occasions and fits into almost every man’s lifestyle. And you can also wear it with just about any attire you own.

Made of durable leather that’s easy to maintain, the Crevo Denham is stark black with a distinctive look.

It’s lightweight and comfortable and features a flexible non-slip synthetic outsole that helps provide all-day comfort. The sole is cozy and comfortable, but not too warm, and provides more than enough traction and proper support.

The Denham also features goring side panels, a burnished toe, and a tab at the back of the boot to make it easier to slip in and out of the boot.

Another thing to like about the Crevo Denham is that it’s among the best affordable Chelsea boots on the market today. You get an excellent boot for the price and one which, with proper care, should last you a long time.

Based in St. Louis and Nashville, Crevo is a division of Elan Polo and markets itself as a footwear company for today’s man. They make boots, sandals, everyday casual shoes, and more, all while keeping up with men’s ever-changing fashion and lifestyle.


  • Distinctive look
  • Affordable
  • Comfortable sole that provides plenty of traction


  • May take a bit of time to break them in

Bottom Line

Whether you’re a man who sticks to a strict budget or not, the Crevo Denham is a good choice. It’s suitable for many occasions and provides both durability and comfort.

Our rationale for choosing these products

“Rationale” sounds a bit formal, perhaps, but the bottom line is that there is a method to our madness for all of our product reviews.

We considered a variety of factors regarding Chelsea boots: Comfort, style, durability, construction, and, as always, the reviews of those who’ve worn them or are still wearing them.

The cost is another factor (and always is), and we try to provide a range of products to cover every man’s

There are a lot of excellent Chelsea boots available, no question. But we think we’ve included something for everyone on our list of the top seven.

Proper care: Be kind to your Chelsea boots (A simple, illustrated guide)

You love the way you look in your pair of leather or suede Chelsea boots. You’re patting yourself on the back for making an investment that’s well worth the price.

But, the next thing you know, your boots aren’t looking nearly as good as they did at first, and it all comes down to this – you’re not taking care of them properly.

Chelsea boots need a bit of TLC to help them look their best every time you put them on and walk out into a new day. Besides, you want them to last a good, long time.

Here are some tips for taking care of your Chelsea boots the right way.

1. Use a boot tree

how to take care of chelsea bootsFirst things first: If you don’t already have a boot tree, it’s time to buy one. A boot tree helps ensure the integrity of the inner leather and insole, while also helping your boots to maintain their shape.

Don’t leave your boots on the floor of your closet or in a box. And you should never store leather boots in plastic bags because the leather needs to breathe. A lack of air may dry your boot out or cause mold.

2. Another word about storing your boots


While it’s wise to store wet boots in a warm area to help them dry them out, never store them directly next to a heat source, such as a radiator. Too much heat makes the leather brittle and may cause cracks later on.

Also, if you don’t wear your boots all year round, never store them for an extended period without cleaning them first. You don’t want salt and other chemicals eating away at them for months at a time.

3. Storing your suede boots


By now, you get the idea – how you store your Chelsea boots is a crucial part of taking care of them and ensuring their longevity. But how you store your suede boots is different from storing leather boots:

  • Store suede boots in a cool place

Never store your suede boots in a place with direct exposure to sunlight. Excessive sunlight will cause the suede to fade while extended exposure to humidity may cause dampness that leads to mildew.

Store your suede boots in a place – such as a clothes closet – where they’ll remain cool and dry.

  • Make sure they’re clean before extended storage

The same rules of proper storage apply to suede boots as they do to leather boots: If you’re planning to store them for an extended period, make sure you’ve cleaned them first.

Even if they look clean, give them a good cleaning anyway, and you may even want to have them professionally cleaned.

4. Cleaning your leather boots


Use a soft brush, preferably one designed for the job, to dust off your leather boots after each wearing.

A stiff brush may scratch and mar the surface. If there are stubborn dirt and debris (or salt rings) on your boots, use a sponge or soft cloth that’s dampened with warm, soapy water and a capful of vinegar to clean the outside.

A quick wipe with a damp cloth is usually enough to get rid of salt stains, but it’s important to address those stains, or any stain for that matter, as quickly as possible.

You may also choose a leather cleaner if you don’t want to try a DIY method.

5. Cleaning suede Chelsea boots


Don’t use water when cleaning your suede boots because water can change the texture and color of the surface. If you spill liquid on your boots, apply a layer of talcum powder or cornmeal after first patting the area dry with a clean cloth.

Allow the layer of powder or cornmeal to set overnight and then use a suede brush to remove it gently the next day.

You can also remove stains from your suede boots by using a kneaded eraser or an emery board to “sand” off the scuffs and stains. If this method flattens the suede, you can bring the texture back by scrubbing with a terry cloth towel, and even a clean toothbrush.

6. Polish your leather boots regularly

how to take care of your chelsea boots 6

Polishing your leather boots at least weekly helps them look well-oiled and clean. The good news is that there’s a wide selection of leather polishes to choose from, and they come in liquid and paste form.

Cover the entire boot surface with the polish, including the sides of the bottom sole. Use a separate cloth to remove excess polish and to buff the boots. Let the boots dry before you wear them again.

7. Use a suede protective spray

how to take care of your chelsea boots 7

A protective spray formulated especially for suede prevents water damage (as well as preserves the suede’s color and texture).

Apply the protective spray all over the boot, but you only need to spray it on lightly because too much could affect the boot’s texture and color.

8. Brushing your suede boots

how to take care of your chelsea boots 8

It’s important to purchase a suede brush to brush out the surface of the suede. You’ll help your boots retain their soft, pleasant texture while helping them to retain their soft texture.

Before brushing your boots, stuff them with crumpled paper to help them retain their shape. Brush the surface gently in the direction of the fibers.

The difference between Chelsea boots and Chukka boots

It’s hard to go wrong style-wise with Chelsea boots or Chukka boots – which we’ll cover in a separate post. Both look good and impress upon others that you know a thing or two about style. It’s safe to say, however, that they’re not the same thing.

Chelsea boots

Chelsea boots have been around a long, long time – since the Victorian era in England, to be exact. The first pair was crafted by J. Sparkes-Hall, the personal shoemaker to the Queen, or so the story goes.

Over 100 years later, Chelsea boots hit a peak of popularity thanks to the 1960s Mod scene in Britain and favored by members of the Beatles and Rolling Stones, among other celebrities.

Chelsea boots are ankle-high and laceless and, in most cases, have elastic panels on either side of them to keep them close-fitting but comfortable.

Some Chelsea boots come with zippers, but they’re easy enough to slip on and off, in any case, thanks to a loop of fabric at the back that you pull.

As with any shoe or boot, getting the right fit is important with Chelsea boots. Make sure that you have enough flexibility in the side panels, but not so much in the instep.

As mentioned, Chelsea boots come in leather and suede models. Leather boots can withstand a bit more wear and tear than suede boots and are your best option during wetter months and periods of weather extremes, such as during the winter.

Excess moisture can easily damage your suede boots.

Black, or navy, is considered the “traditional” colors of Chelsea boots, but they also come in virtually every color.

The Chelsea boot, like the Chukka boot, is versatile enough to fit with a variety of items in your wardrobe. Chelsea boots are good for most occasions, including dressier outings. They’re also a good option if you work in a more formal office setting.

Chukka boots

Chukka boots also have an interesting history; British soldiers – and other soldiers of the allied troops – wore them in World War II for marching through desert terrain. Hence, they’re also known as desert (or turf) boots.

Chukka boots are distinctive for their ankle-length and pairs of eyelets for laces. They have a classic, toe design, and open lacing system.

Many Chukka boots consist of suede or calfskin, although leather is used too, especially for use during the winter months when durability is important.

If you’re looking for a more casual look, then Chukka boots are a good choice.

The soles of many Chukka boots are thicker than traditional footwear soles, which, again, makes them better-suited for casual occasions, but they also come in thinner soles, which give them a finer look.

Chukka boots work well with almost any style, although fashion experts say they look better with narrow-legged pants. While the uppers usually come in suede or calfskin, soles of Chukka boots are made from rubber. Both sections tend to come in contrasting colors.

Your Chukka boots should have a light, comfortable fit as long as you’ve sized them correctly.

A true desert boot shares the same style of lacing as traditional Chukka boots but come in a slightly different style.

For one, their sole is made of a strong rubber material instead of leather, while the stitching around the sole isn’t as visible as it is with a Chukka boot. That’s also one reason why they have a more casual look.

In case you were wondering, the word Chukka comes from the game of polo, in which Chukka refers to a period of play (at least you’ll have the answer if the question comes up at a cocktail party).


What are your thoughts? Do you wear any of the brands listed in this article? Do you prefer other brands? We’d love to hear from you and always welcome your comments and suggestions.


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About The Author

Domen Hrovatin
Domen Hrovatin

Domen—a self-confessed facial hair addict—is a grooming professional, style enthusiast, and someone with deep personal experience and knowledge about male pattern baldness. His work was mentioned in countless notable men's grooming and style publications, including Beardbrand and AskMen.

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