Best Men’s Chelsea Boots: Top 20 Brands Reviewed In 2020

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Chelsea boots are a versatile boot that can really amp up your style.

However, when selecting the best Chelsea boots, you need to find a pair that is not only crafted from quality materials (i.e. leather or suede), but also has a color to match your style, the right ankle closure, appropriate heel height, and has an universal outsole stitching that can be easily repaired over the years – like the Bitflex Chelsea boot.

In this review and guide, we not only take a look at some of the most popular Chelsea boots currently available on the market, but we also walk you through important considerations you should think about before making your purchase, along with our quick and easy-to-remember guide on how to care for your new Chelsea boots.

Let’s get started:

Everything You Need To Know Before Buying New Chelsea Boots

As we researched all the different Chelsea boot brands available, we found that eight key factors were important when selecting the best Chelsea boots for you.

Here’s what they were:

1. Material

One of the most important decisions when buying a quality pair of Chelsea boots will be the material that it’s made from.

Before making your purchase, it’s imperative that you look at the type of leather, suede or other materials that were sourced when buying a Chelsea boot.

Buying a Chelsea boot made from a poor-quality material will not only cause the boot to fall apart quickly, but it will also look bad after only a few months of wear.

Here’s a quick primer on the different types of leather to be mindful of when buying Chelsea boots:


Finding the perfect leather Chelsea boot isn’t nearly as easy as one may think.

A quick search of any online retailer and you will find that Chelsea boots come in a variety of different leather types which include the following:

  • Top grain
  • Full grain
  • Genuine leather
  • Calf leather

Here’s a quick overview of how each of the following leather types differ:

Top Grain

The nicest of all the leather varieties, top grain is a sanded or buffed-down outer part of the cows hide.  It not only looks the nicest but will also develop a very nice patina over time.

This leather variety is absent of any surface imperfections and is one that will last for decades.

When looking for top grain leather Chelsea boots, expect to pay several hundred dollars.

Full Grain

Full grain, much like top grain, contains the outermost layer of the hide.

However, full grain also goes much deeper into the hide as well.  This naturally thicker leather, while stronger than top grain, does contain surface imperfections.

Therefore, if the cow that this leather was sourced from was substantially older, this leather type may contain a more wrinkled and weathered surface.

While this leather variety may work for a wallet, it’s thicker and rougher texture is not good for the sophisticated Chelsea boot.

In addition to how a full grain leather will visually work, it is also a bit more rigid which will take a bit longer to form to the natural contours of your feet – and in turn, may cause some blisters when first wearing your new boots.

Genuine Leather

While genuine leather may sound fancy, it isn’t.

Genuine leather is made from the leftover bits of the hide that have been bound together with glue.  Susceptible to stretching and tearing, we only recommend genuine leather if you are on a strict budget or simply want a Chelsea boot for one or two years.

While still polishable, expect the boot to crack or dry out if worn for several years.

Calf Leather or Calfskin

One of the highest quality leather grades that you can find for Chelsea boots will be calf leather, sometimes also referred to as calfskin.

This leather has been sourced from calves (young cows) and has a fine, almost velvet, feel to it and is extremely elegant.

While some men may be turned off by the thought of buying calfskin Chelsea boots given the animal they were sourced from, it’s important to note that the calfskin is a byproduct for harvesting veal.

Therefore, Chelsea boots are only one of the many uses that the animal has served.

Like top grain leather, calf leather will last for decades and develop a nice patina with time.


Used from the underside of the skin rather than the outer layer, suede is a texturally different material from leather.

While not nearly as durable as leather, the textured surface will feel much softer.

Given that suede isn’t as durable, it is subject to both tearing and breaking down with time.  Unable to be polished either, you can expect a pair of Chelsea suede boots to only last you a few years at most (with regular wear) before needing to be replaced.

Suede vs. Leather Chelsea Boots?

Comparing suede vs. leather Chelsea boots is like comparing apples to oranges.

If you want a soft and textured looking boot, go with suede.

However, if you want to purchase a pair of Chelsea boots that will last you for several years and will look both classic and stylish, then go with a boot made from either top grain or calfskin leather.

They will develop a nice patina and be extremely versatile with your existing and future wardrobe.

2. Color

While we normally think of boots coming in either two colors, brown or black, you will quickly find when researching Chelsea boots that you can find them in a multitude of colors which includes the following:

  • Tan/Beige/Sand
  • Black
  • Brown
  • Blue
  • White
  • Grey/Stone

So, which one should you get?

While stone or grey may be trendy right now, a darker brown or black Chelsea boot will always remain timeless.

Our best recommendation here is for you to ask yourself whether you are buying a boot only for the season (then it’s fine to go with a trendy color) or if you want a Chelsea boot that you can wear for the next 10 years (then we recommend to go with a neutral and classic color).

3. Ankle Closure

Chelsea boots come with two main side closures:

  • Slip-on / Elastic
  • Zippered

Here’s a quick bit of information on each:

Slip-On / Elastic

By far, the most popular side closure when it comes to Chelsea boots will be the elastic band closure.

This allows for a better range of motion when it comes to walking and ankle mobility while keeping the boot secured to your feet.

The elastic band is also considered to be the more classic of the two closure systems.

Whether you are wearing dress pants or denim, the elastic closure can work with both.


While zippers can be found on higher or mid-calf boots, when it comes to Chelsea boots, they are not all that common.

Unlike the elastic band that provides a little extra movement with your feet, the zipper will allow the boot to feel a bit more secure.

However, one major drawback to zippered Chelsea boots is their tendency to get jammed due to dirt and debris that may be kicked up from the ground when walking.

If you are looking for a boot to last you for years, the slip-on or elastic ankle closure may be a better pick here.

4. Heel Height

As you will see in our reviews below, most Chelsea boots have a rather short heel that is akin to most work boots.

At only a fraction of an inch, the heel won’t be too noticeable when walking.

However, we did find during our research that some Chelsea boots do have what is called a Cuban heel.

Cuban heel Chelsea boots are raised about 1.5″ and can give you a much taller appearance.

The Cuban heel is often found on cowboy boots (source) and has a slightly tapered cut.

Some political-savvy readers may recall when the Cuban heel made national headlines during the 2016 election.  Senator Marco Rubio was spotted (and teased) for wearing a pair of Florsheim zipper boots.

Unless you plan on running for president, be it cowboy or Chelsea boots, it is completely okay to wear a raised heel boot to gain a bit in height.

5. Repair

With some stylish Chelsea boots costing a few hundred dollars, it only makes sense that you want to make sure that they will last for years and not just a single season.

If you are thinking about buying a Chelsea boot that is crafted from quality materials, one trademark sign that you will want to look for is the outsole stitching.

Boots come in two primary stitching types:

  • Goodyear
  • Blake

While Goodyear is widely considered to be a much stronger and durable stitch (source), the Blake stitch is still a worthy alternative.

Shoes relying on either one of these stitches can have their outsoles (bottom of the shoe) repaired when worn down.

Not only does this lengthen the life of the shoe, but it is also an easy way to see the quality of the craftsmanship itself.

6. Sizing

During our research, we found that most Chelsea boots tend to run about a half-size smaller than your standard tennis or casual walking shoe.

Given that Chelsea boots don’t have a lace closure that can close the gap between your foot and shoe to prevent rubbing, you will want to be careful about this.

In addition to talking a half size off, we strongly recommend that you also read the company’s product description and reviews regarding overall fit.

7. Price

As is the case with all footwear, prices can vary depending on a variety of factors.

While we highlighted all the key buying considerations above, the brand of the boot itself can also largely dictate how much you pay for a good pair of Chelsea boots.

However, after researching a multitude of boots on the market, we found that the sweet spot for a good (not great) pair of Chelsea boots should cost you around $125.

If you want a pair of Chelsea boots made from top grain or calf leather, along with a quality outsole stitching, then you should expect to pay anywhere between $200 and $400.

Paying more than $400 typically doesn’t yield any great advantages when it comes to durability or craftsmanship.  Instead, you will likely be paying a premium for the brand name itself.

20 Best Chelsea Boots For Men Reviewed 2020

1. Rhodes Footwear Huxley Boot

When it comes to quality Chelsea boot brands, Rhodes Footwear is among the best.  Striking that perfect balance between both fashion and function – they Huxley Boot is a classic Chelsea boot will quickly become a wardrobe favorite for many.  Relying on a premium calf leather upper, it will be both intensely durable and breathable.  But what sets this boot apart from many others on our list is the anti-shock insole that is relying on Texon that some claim, is like walking on clouds.

One nice feature that men really like about this boot is the welt.  Relying on a Blake stitching, the outsole can easily be replaced.  Therefore, if the leather upper remains in good shape (assuming you do proper leather cleaning regularly), then once the outsole begins to wear down, you can bring these to your local cobbler to have them repaired.

Overall, the Rhodes Chelsea boot is a great and stylish pick.  Available in a variety of sizes and colors – you should have no problem finding the perfect one for you.

Read hundreds of other reviews here.

2. Red Wing Heritage Weekender Chelsea Boot

Known for their premium leather goods, Red Wing Heritage sets the standard of which all other leather good companies are compared.  While most Chelsea boots are made for more sophisticated or formal wear, Red Wing Heritage decided to go against the grain and offer up an ultra-comfortable, yet still stylish, weekender Chelsea boot.

Still relying on that classic full-grain leather that we have grown to love in many products from Red Wing Heritage, you can expect the leather uppers on this boot to last you for years.  When cared for properly, the leather will also develop a nice patina with time.

Underneath the shoe, you have a textured outsole that provides a great grip in slippery conditions.  Relying on a stitchdown construction, the outsoles can be replaced when worn down – greatly extending the life of the boot.

Read hundreds of other reviews here.

3. Aldo Men’s Delano Chelsea Boot

Aldo’s stylish designs and reasonable price points have taken the contemporary shoe world by storm.

The Delano Chelsea boot is a great example of why this brand is so appealing. These lightweight leather boots are ideal for both Spring and Fall due to their breathability.

The tastefully rounded toe, elastic inserts, and back loop are all great—albeit, classic—features of these boots. Available in shiny black and smooth cognac, this boot walks the line of casual and cool with ease.

Read hundreds of other reviews here on Amazon.

4. Bitflex Chelsea – Astorflex

For all the eco-friendly gents out there who make sustainable fashion a priority, it’s your lucky day! The Bitflex Chelsea boot is everything you’re been looking for and so much more.

Handcrafted by master shoemakers in Northern Italy, these guys have been making killer shoes for over 6 generations. I think it safe to say that these guys know what they’re doing.

These boots are made from premium European leather that is aged to perfection for 30 days. They are then softened into a supple suede and mounted on a 100% natural rubber sole for the perfect balance of style and comfort.

Read hundreds of other reviews here.

5. Dockers Men’s Badger Chelsea Boot

Over the years, Dockers has become a respected name in casual apparel and footwear.

The ‘Badger’ Chelsea boot has got loads of old-school charm with all the added bonuses of contemporary design. The burnished full-grain leather and clean lines make this pair of boots ideal for casual everyday wear.

The flexible construction and cushioned latex foot bed are sure to provide exceptional comfort. Finished with vintage-inspired details like contrast stitching and a stacked heel, you’ll be ready to take on the day and dance through the night.

Read hundreds of other reviews here on Amazon.

6. Brook Brothers Chelsea Boots

Made in Italy, these tonal stitched Chelsea boots by Brook Brothers offer a classic yet elegant style.  With their slightly moderate ankle height, they won’t rub awkwardly on your leg while still providing adequate support.

Available in several sizes and two colors (brown or black), they will be a versatile boot to add to your wardrobe.  Crafted from full grain leather, they should last you for years while developing a nice patina with time.

Some men do note that these do run a bit smaller, so you may want to size up just a half-size to account for this.

Read hundreds of other reviews here.

7. GLOBALWIN Mens 1638 Chelsea Boots

If leather products aren’t your thing, but you’d still like to find the perfect ankle boot—Globalwin’s Chelsea boot may very well be for you. This low-cut ankle boot packs quite the punch and comes in four versatile colors—brown, grey, tan, and black.

The two-eyelet lace-up design and elastic stretch panels allow for easy on/off. Complete with a cushioned footbed for added comfort and contrast stitching for added style, it’s hard to go wrong with this fashionable boot.

Read hundreds of other reviews here on Amazon.

8. Grantland Waterproof Chelsea – Cole Haan

If you’re committed to the idea of adding a waterproof boot to your closet with a less “sleek” and more “rough and tumble” vibe, then Cole Haan’s Grantland Chelsea boot has got your back.

These waterproof boots are crafted from rich oil-tanned leather and mounted on a solid recessed lug sole for the ultimate traction on bad weather days. Designed using the same technology as the Warren boot, these guys strike an impressive balance between comfort, durability, and wearability.

Read hundreds of other reviews here.

9. Guess Men’s Jibbs Chelsea Boot

For all the guys who love to stay on top of the trends, the Guess Jibb’s Chelsea boot will get you exactly where you want to be.

Since the early 80’s, Guess has been a highly sought after name in both men’s and women’s fashion. In recent years, they’ve really hit the nail on the head when it comes to their footwear. The ‘Jibb’s’ boot is no exception!

This suede boot features the usual slip-on design complete with a classic logo plaque. Planning a weekend getaway? Well, the good news is these are the only pair of shoes you need to bring!

Read hundreds of other reviews here on Amazon.

10. Massimo Matteo Chelsea PT Boot

Is ‘sophisticated’ your middle name?

Well thanks to Massimo Matteo’s Chelsea PT boot, it is now!

Crafted in Brazil from premium leather, you’ll want to reach for these all year long. The straightforward design and classic round toe are well-complemented by the slightly textured outsole.  The elastic side panels make for an easy, snug fit and the soft leather lining adds a welcomed boost in comfort. Available in neutral options of brown or black, but also black with contrast elastic and soles in red or blue if you’re looking to make more of a statement.  Slipping on an awesome pair of boots has never been easier!

Read hundreds of other reviews here on Amazon.

11. Rodd & Gunn Suede Chelsea Boots

Whenever I’m looking to add some color variance to my closet, a bold pair of shoes is usually my method of choice.

Rodd & Gunn’s Westholme Suede Chelsea Boots come in a tastefully smokey grey that’ll have you looking like you just got off work at the coal mine—the wall street equivalent of a coal mine that is.

Their sleek granite color and smooth silhouette make these top-quality Chelsea boots a stylish pick if you’re looking for a welcomed change from the usually black or brown. Made in Portugal with a gorgeous upper and sturdy soles, these boots are sure to keep you lookin’ spiffy for many years to come.

Read hundreds of other reviews here.

12. Aquatalia Adrian Leather Chelsea Boots

The masterful Italian shoemakers at Aquatalia have bestowed upon us a one-of-a-kind Chelsea boot. These polished leather boots embody the ultimate in rugged sophistication.

These shoes are constructed with a luxurious deep brown leather upper and set on a sturdy heel and well-crafted sole. Details like the water- and stain-resistant finish and elastic goring for quick on-and-off make these perfect for men on the go.

Pair with a slim cut trouser and your favorite button down and you’ve got a versatile look that can transition effortlessly from day to night.

Read hundreds of other reviews here.

13. Roskilde Chelsea – Duckfeet

It would seem that Europe is eons ahead of everyone else when it comes to craftsmanship and design. The Danish shoe company Duckfeet exemplifies this superior construction like the best of ‘em!

With the natural shape of a foot in mind, their Rockslide Chelsea boot was built for exceptional comfort. Every boot is made from eco-friendly Terrace leather that is handcrafted in Germany.

Complete with the traditional elastic side inserts, this rugged take on the traditional Chelsea boot will keep you roaming through the wilderness is style. Set on a crepe rubber sole and complete with double natural stitching, these are a fantastic pick for anyone looking for both strength and detail.

Read hundreds of other reviews here.

14. Sperry Top-Sider Flex Deck Chelsea

Sperry’s Top-Sider Flex Deck is a Chelsea boot like you’ve never seen it before.

More akin to a rain boot, these babies will be sure to keep you dry and comfortable. Whether you’re caught in the rain or spending a day near the sea, you can rest assured due to their durable and 100% waterproof exterior.

The cozy micro-fleece lining and supremely cushioned footbed will keep you comfortable from above and below. As if that wasn’t enough, the uniquely patterned sole provides amazing traction on both wet and dry surfaces—a necessity for every outdoorsy fellow.

Read hundreds of other reviews here on Amazon.

15. Steve Madden Men’s Hibrid Chelsea Boot

Since its inception in 1990, Steve Madden has been at the forefront of the shoe industry from day one.

Praised for his undeniable ability to transform high fashion trends into wearable footwear for every occasion; the Hibird Chelsea boot speaks to all of the progressive thinking we’ve come to know and love.

The hallmark of this handsome boot is most definitely the toe shape—not quite round and not quite square looks like it’s the perfect place to be! The result is an elegant boot with a European flare.

Read hundreds of other reviews here on Amazon.

16. Suede Chelsea Boots – Brooks Brothers

Anyone looking for a classy boot to add to their closet should virtually make their way on over to Brooks Brothers and grab a pair of Suede Chelsea boots.

These guys rarely miss a beat when it comes to crafting quality shoes. Their take on the Chelsea boot is made from a buttery brown suede and leather soles.

Complete with tonal stitching and a perfectly rounded toe, these are the ultimate statement boots! Whether you’re roaming through city streets or headed on a fall vacation with your sweetheart—these top-rated Chelsea boots will definitely not disappoint.

Did we mention they’re imported from Italy? Enough said.

Read hundreds of other reviews here.

17. Warren Waterproof Chelsea – Cole Haan

Anyone who’s ever been caught in a torrential down poor knows that these unexpected showers can be the death of your favorite leather shoes.

Thankfully, Cole Haan’s Warren Waterproof Chelsea is just what you need to carry you through the rainy season. These flawlessly crafted boots are sure to be a practical addition to any man’s shoe arsenal.

The Warren Collection was designed using cutting edge technology to reduce weight while adding flexibility and comfort. They’ve also upped the ante with a sole that offers superior traction in an agile yet stable package.

Read hundreds of other reviews here.

18. Williams Welt Chelsea – Cole Haan

It looks like the design team down at Cole Haan has done it again with the Williams Welt Chelsea boot!

These top-rated Chelsea boots are comprised of high-quality suede and leather uppers as well as a heavy-duty leather storm welt. Let’s just say that it sounds like these boots are made to last. The cushioned footbed and leather sock lining are sure to keep even the burliest of feet happy.

Read hundreds of other reviews here.

19. Wolverine Bedford Chelsea Boot

If you’re looking for an understated Chelsea boot that oozes casual luxury then do yourself a favor and slip your feet in the Wolverine Bedford Chelsea boot.

Where do I even begin with these beauties?

It should be mentioned that these classy Chelsea boots bring to mind an effortless masculinity reminiscent of the Marlboro Man. The rich color of the full-grain brown leather has a perfectly aged look and can be easily dressed up or down.  However, these boots are also available in black. If comfort is a must have, then you’ll be sure to appreciate the trademarked-technology anti-fatigue footbed —not to mention the moisture-wicking lining! A durable slip-proof outsole provides stellar traction for wet or icy weather, making these a perfect choice for the cooler months.

Read hundreds of other reviews here on Amazon.

20. Bruno MARC BERGEN-05

Bruno Marc New York serves up their version of the Chelsea boot with some much-welcomed deviations from the classic style.

Comprised from premium faux-leather, this boot is sure to appeal to men who want some serious mileage in the style department. The wingtip detailing gives these contemporary boots a vintage feel. Dress them up or down for an understated elegance.

There’s a very good chance you won’t want to take them off thanks to their cushioned latex footbed and durable rubber sole.

Read hundreds of other reviews here on Amazon.

How And What To Wear Chelsea Boots

One of the great advantages of adding a pair of Chelsea boots to your wardrobe is their versatility.

Easily able to be dressed down for casual occasions and dressed up for the more formal or business occasions, you can make them effortlessly work for you.

Here are a few scenarios, along with clothes you can put on when wearing your new Chelsea boots:

Casual attire

With a pair of skinny denim jeans along with a white t-shirt or button-down, a stylish pair of brown Chelsea boots can make it work.

Some men also do like to wear a pair of suede Chelsea boots with the above clothing as it further demonstrates a more relaxed look.

Smart Casual Attire

Kicking things up just a bit, a pair of classic Chelsea boots in brown, tan or black can complement a smart, casual style.

Whether it’s in a relaxed office setting or going out for a date on a Friday night, a neutral-colored Chelsea boot along with a blazer, button-down and jeans or chinos will look great.

Just be sure that if you go with this look, try and match your belt to your Chelsea boots for color coordination.

Business and Semi-Formal Attire

From a casual attire, as outlined above, to a business or semi-formal setting, a calfskin or top grain leather Chelsea boot can span all settings.

When it comes to business, if you are wearing a blazer, button-down and either chinos, khakis or even dress pants, Chelsea boots can complement them effortlessly.

Even when checking out popular hashtags such as #chelseabootsmen or simply #chelseaboots, you can see men pulling off this look with absolute ease.

How To Care And Maintain Chelsea Boots

Caring and maintaining your Chelsea boots is just as important as finding the perfect pair.

The last thing you want is to have your top grain leather Chelsea boots look and feel bad after they get wet a few times.

Therefore, we wanted to put together this handy six-step guide on how to care for your Chelsea boots:

1. Dry with a towel

When it comes to drying your Chelsea boots, particularly those that are made from either leather or suede, it’s important that you do so carefully.

While it might be tempting to toss your Chelsea boots underneath or on top of a radiator or heater within your house, resist the urge.

Placing your Chelsea boots on or around a heat source can dry out the natural oils found within the leather and cause them to prematurely crack.

Instead, you will want to go ahead and make sure that you just get some paper towels or a hand towel and dry your boots off fully.

You don’t really have to worry about the outsoles here; they were designed to get wet. Just be sure that you wipe down the leather uppers.

2. Clean leather Chelsea boots properly

If you intend on wearing your Chelsea boots within the next few days, then simply wipe them down with a damp cloth (after you had dried them) in order to remove any residual salt or other minerals that may rest on the surface.

Should you be storing your Chelsea boots for the summer or simply don’t plan on wearing them for the next couple of weeks, then you will want to give them a slightly deeper cleanse and conditioner (more on this on step 4).

Clean with the right tools

When it comes to cleaning your leather boots, you just need to follow these four steps:

  1. Remove the laces
  2. Give the boots a thorough brushing with a fine horsehair or boars hair comb to remove clumps of dirt or other gunk
  3. Wipe down with a damp cloth of warm water
  4. Use saddle soap to fully remove leather destroying minerals

3. Clean suede Chelsea boots properly

Caring for suede is much different than cleaning with leather.

Whether you plan on wearing your boots in a few days or further down the road, you will want to follow these steps to ensure that your boots retain their look the next time you plan on wearing them:

  1. Remove the laces
  2. Use a suede brush to remove stubborn scuff marks
  3. Use a spray designed specifically for suede in order to retain the texture and look

4. Conditioning your leather Chelsea boots

While heat is one of the biggest environmental factors that can destroy a beautiful leather Chelsea boot, another large problem is neglect.

All too often, men will pay top dollar for a quality pair of Chelsea boots only to have them look crummy a few months after wearing them.

One common problem that many men have when it comes to maintaining their leather goods is not conditioning them regularly.

Whether it’s your leather messenger bag or leather Chelsea boots, they need to get conditioned regularly.

One product we’d like to recommend that men check out is Leather Honey Leather Conditioner.

Using this product is effortless.

Just follow these steps:

  1. As outlined in step 1 above, give your Chelsea boots a good deep cleanse
  2. Remove the laces
  3. Apply the leather conditioner to your Chelsea boots with a lint-free microfiber cloth
  4. Apply to all the leather upper of your boot
  5. Let it sit overnight
  6. Wipe off excess with a clean microfiber cloth

This will help ensure that the leather retains its natural oils while also helping to develop a nice patina.

While you can do these steps any time during the season when wearing your Chelsea boots, we also highly recommend that you do this before storing them away for the summer as well.

6. Boot tree to maintain shape

Boot trees may seem like an ancillary purchase that isn’t necessary, especially when it comes to a calfskin leather boot.

However, this couldn’t be further from the truth.

Boot trees play a key role in not only helping the boot to maintain its shape when it’s not worn but will also wick away any excess moisture that your sweaty feet may have left on the insides.

Effectively, this helps to prevent your leather Chelsea boot from destroying itself on the inside.

You can get a decent wooden shoe tree for under $50.

It’s an investment that we think is worth the money, especially if you plan on getting a pair of Chelsea boots for $200.

Questions Men Had About Chelsea Boots

What color Chelsea boots should I buy?

As we eluded to previously, the color of the Chelsea boot you plan on buying is a personal choice.

Classic colors such as tan, black or brown are timeless and can work with many different outfits.

Whether you are going super casual or semi-formal, these neutral colors can work without a problem.

Bold colors such as red, stone or even grey are trendy and should only be purchased for a season or two at most.

When do Chelsea boots go on sale?

With a good pair of Chelsea boots costing upwards of $400, it only makes sense that you would want to pick up a pair when they are on sale.

Based on our research, we found that most Chelsea boots tend to go on sale after the holidays and even in February or March with the end of season sales.

Are Chelsea boots formal?


Black and brown top grain polishable leather Chelsea boots with an elastic band ankle can be worn to a semi-formal setting.

Do Chelsea boots run big?

Quite the contrary.

We found that most Chelsea boots tend to run about a half-size smaller than your typical shoe size.  We recommend that you always check with the product description or reviews left by other men when finding the appropriate size for you.

What type of sock should you wear with Chelsea boots?

Dress socks work the best here.

While Chelsea boots are cut high and your ankle or lower calf is rarely seen, even when crossing your legs, a mid-calf dress sock can help to prevent any irritation should the back of the Chelsea boot rub against your skin when walking.

Where can you buy Chelsea boots?

Chelsea boots can be found in a variety of retailers and directly from companies.

Here are a few of the more popular outlets we recommend that you check out:


Direct from Companies

Chelsea Boots vs Rock ‘N Roll Boots vs. Chukka Boots

One common point of confusion from both novice and men who are familiar with the nuances of fashion is the differences between Chelsea boots, rock ‘n roll boots and chukka boots.

Here’s a brief overview of each of these three easily confused categories:

Chelsea Boots

As seen in both our review and guide about Chelsea boots, they are often made from either leather or suede and are paired with an elastic or zippered ankle closure.

What sets Chelsea boots apart from both rock ‘n roll and chukka boots is that they can be paired with a wider variety of fashion choices.

Whether you are planning to wear a casual denim and button-down t-shirt outfit or are taking it in the opposite direction and going more formal with a blazer and dress pants, Chelsea boots won’t be out of place.

Thanks to their lack of laces coupled with a narrow toe-design make them extremely versatile, especially when compared to other common boot types.

Rock ‘N Roll Boots

Popularized with the great British invasion of the 1960s (i.e. the Beatles, the Rolling Stones, the Kinks, etc.), Rock ‘N Roll boots carry with them a very familiar design as the Chelsea boot and are rightfully confused.

Perhaps the biggest difference between both the rock ‘n roll boots compared to Chelsea will be their highly polished leather, a zipper ankle closure, and in some cases, coupled with a decorative chain or rink around the ankle.

Made for performance, the Rock ‘N Roll boot is typically always black and has a very polished look.

More of a sub-genre rather than its own unique shoe category, Rock ‘N Roll boots are often bucketed in with Chelsea boots when shopping online.

Chukka Boots

Equally as popular as a Chelsea boot, chukka boots are a rounded and laced boot that comes in either a leather or suede material.

Their rounded toe cap and shorter cut (just around the ankle bump) give them a much more casual look that is great for daily wear.

In office settings where a more relaxed smart casual is worn daily, chukkas are a great way to demonstrate your sense of style without drawing attention.

To further lend to their sense of comfort, chukkas also often have both chunky insoles and outsoles – making daily walking in them much more welcoming.

How we found the best Chelsea boots

When we set out to find the best Chelsea boot for men of 2020, we thought it was going to be an easy task.  But we quickly realized that the variety of Chelsea boots available was massive.

From Chelsea boots that were budget-friendly to those that relied on only the finest materials and employed expert craftsmanship, we feel confident that our list above provides plenty of great picks that can work within your budget.

We hope that this review and guide of Chelsea boots helped in finding the perfect pair for you!

About The Author

Shawn Burns

Shawn is the founder and senior editor at Tools of Men, the leading style and grooming source trusted by men in 187 countries. He started this site with the goal of teaching men proper grooming habits and sensible style. He is an expert in all things men's grooming related. His work has been mentioned on countless sites including The Wall Street Journal, NBC, AskMen, Vice, WikiHow, and the New York Times.

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