Articles,  Style guide

Best Men’s Chelsea Boots You Can Buy in 2023

  This post may contain affiliate links. If you click on a link and make a purchase, we may earn a commission at no additional cost to you. Learn More.  

Chelsea boots are incredibly versatile and timeless. They are versatile because the right pair of Chelsea boots can be worn with jeans all the way up to with a suit. They are timeless because they were in style decades ago and will remain in style for decades to come. As such, Chelsea boots can play a central role in your wardrobe. Here is a list of the best Chelsea boots for men ranging from affordable to more high end.

The Best Chelsea Boots for Men

Best Affordable Chelsea Boots ($100 and below)

It’s hard to find a high quality chelsea boot or any boot for that matter in this limited price range. But if you are experimenting with your personal style and want to find out if a chelsea boot would work for your style then this can be a good option.

If you don’t know whether you will like this style or not, there is no point in investing in a $400 boot which you will rarely wear. Just keep in mind that you cant expect these bootss to last more than a couple of seasons or go through multiple resoles. With that out of the way, let’s get in to the best affordable Chelsea boots.

Clarks Paulson Chelsea Boot

These Clarks Paulson Chelsea Boots come in leather and suede as well as a multitude of different colors, so you can find one that suits your personal style. They feature decent quality leather and suede uppers along with grippy rubber outsoles. To enhance comfort these have a Ortholite footbed which will makes them great for prolonged wear.

The shape of these Chelsea boots is also quite modern which makes them quite versatile. You can pair these with jeans and chinos as well as with business casual outfits.

Kenneth Cole Ely Chelsea Boot

If you’re looking for an affordable Chelsea boot that you can wear in more formal settings, then these Kenneth Cole Ely Chelsea boots are a great option. These have a really attractive streamlined design which makes them pair really well suits and dress pants. The brown color is incredibly versatile which allows you to wear them with both suits as well as jeans.

They also feature a rubber outsole for grip as well as comfortable insoles and a gel pod cushioned heel to help with comfort.

Kenneth Cole Tully Chelsea Boot

These Kenneth Cole Tully are a unique take on the Chelsea boot. Chelesa boots typically have the elastic panels on both sides of the boot which ends before the heel. But on these boots the elastic panel actually wraps around the top portion of the heel which makes them slightly easier to get on as well as unique.

These boots have a really slim silhouette which makes them quite reminiscent of the Saint Laurent aesthetic. So if you don’t want to spend $1000 plus on a pair of Chelsea boots, consider these since they offer a similar style but at a fraction of the cost.

These boots also feature a gel pod heel as well as 37.5 technology that should keep your feet dry and comfortable as well free from odour.

Amazon 206 Collective Chelsea Boot

Amazon recently introduced their own line of footwear called the 206 Collective which includes a Chelsea Boot. The boots feature a leather upper along with a crepe rubber outsole similar to those found on Clarks Desert Boots. The boots currently come in two colors; black and dark brown.

The silhouette of the boots is quite relaxed which makes these great for casual wear. These are a great starter Chelsea boot because they come in at around $65 which is a great price for a Chelsea boot with a leather upper and durable outsole.

Best Chelsea Boots under $200 ($180 to $250)

This is a really interesting price range because you start entering the world for good quality boots that feature good quality leather/suede and a solid construction. These boots are definitely superior in both style and construction to those in the 100 and below range. You can expect to have these boots for at least a couple of years and actually go through a couple of resoles.

Thursday Boots

Thursday Boots is a great company to consider for quality yet affordable footwear. They gained a lot of popularity due to their best selling captain boot but these days they offer many different styles of men’s shoes. Thursday has three offerings when it comes to their Chelsea boots; the Duke, Cavalier and Legend.

The Legend Chelsea boot is a rugged interpretation of the Chelsea boot featuring a thick rubber outsole and a durable leather/suede upper. These boots are perfect replacements to Blundstone Chelsea boots because they offer enhanced durability but with a much more stylish aesthetic.

The Cavalier Chelsea boot is personally my favorite because it is the dressiest of all the Chelsea boots Thursday offers. The Cavalier is incredibly streamlined with a more elongated and sleeker toe box which makes it perfect for dressier occasions. I own the Cavalier in the shadow gray color and it looks amazing with jeans, chinos and khakis.

If you want a Chelsea boot that you can dress up or down with ease, then consider the Duke. This was the first Chelsea boot introduced by Thursday Boots and it has maintained its popularity ever since. The Duke is not as sleek as the Cavalier but it is also not as utilitarian looking as the Legend but falls right in between. It is sleek enough to wear with business casual outfits but also works incredibly well with chinos, jeans and a casual jacket.

Beckitt Simonon

Beckitt Simonon has gained a lot of popularity recently in the menswear community for affordable and quality footwear. They offer two different styles of Chelsea boots; The Bolton and Preston. Both feature a blake stitch construction which makes their shoes relatively streamlined and slim.

The Bolton features a more slimmer shape therefore it is the dressier Chelsea boot perfect to pair with suits and business casual outfits.

The Preston on the other hand is not as slim and is perfect for business casual and sharp casual style. Think of the Bolton as being similar to the Cavalier by Thursday while the Preston is more comparable to the Duke.

Oliver Cabell Chelsea Boot

If you’re looking for a unique and well made Chelsea boot then definitely consider Oliver Cabell. These boots come in a beautiful sand colored suede from Italy which is both soft and durable. Unlike the Thursday and Beckitt Simonon Chelsea boots which feature either a leather or rubber outsole, these Oliver Cabell’s come in a stitched crepe outsole which makes them inherently more casual and relaxed. As such, these would work really well if your personal style leans more on the casual and street casual side of the spectrum.

Best High End Chelsea Boots ($300 and up)

This is where you get into high quality footwear featuring premium leather and suede uppers as well as excellent construction. Simply put, you can expect these boots to last many years if not decades with proper care and maintenance. These shoes are a great option for men who find that the Chelsea boot really suits their personal style and they now want to invest in a Chelsea that they can have for many years.

R.M Williams Chelsea Boots

R.M Williams boots are incredibly popular in Australia and that popularity has expanded worldwide. The most iconic style they offer is their Crafstman Chelsea Boot. These boots come in high quality leathers and you also have the option of choosing either rubber or leather soles.

Leather soles are going to be dressier but if you plan on wearing these boots day in and day out, then rubber would be a better option due to more grip and enhanced durability.

Whichever model you choose, with R.M Williams you’re getting an incredibly high quality pair of boots that should last at least a couple of years if not decades with proper care. Another proof that these boots are meant to last many years is that R.M Williams offers an in house shoe resole and repair service which is highly recommended when your boots need a resole.

Carlos Santos Chelsea Boots

Ask any shoe aficionado about Carlos Santos and they will tell you that they make some great shoes. The price to value ratio for Carlos Santos shoes is remarkable and this is partly due to the fact that they are made in Portugal (unlike Italy or Spain) where production costs are relatively lower. But don’t for a moment think that these are any less quality than shoes coming from Spain or Italy.

These Carlos Santos Chelsea boots feature a durable goodyear welt construction and a hand painted and patina leather upper. The boots are incredibly well designed with great proportions which makes them sleek and modern without sacrificing comfort. The best part is, their patina service allows you to choose from a multitude of different leather colors which truly allows you to get a boot that is as close to custom as you can get in this price range.

Carmina Chelsea Boots

Carmina is an incredibly well renowned shoe maker from Mallorca Spain. They have been making shoes for over a hundred years and the business is still a family owned enterprise. Carmina shoes are very well respected on shoe blogs which goes to show that they offer a very high quality product.

Their Chelsea boots are available in a number of different leathers, colors and lasts (shape of the shoe/boot). Carmina is well known for making durable shoes that can last for many years if not decades. Their shoes typically feature a goodyear welt construction which means you can have them resoled multiple times. The leathers and suedes they use are all from premium tanneries which means these shoes only get better with wear and age.


I hope you enjoyed this list of the best Chelsea boots for men. Of course there are hundreds of Chelsea boots to choose from but the purpose of this article was to give you multiple options ranging from affordable to high value and finally to more high end boots.


Are Boots Business Casual?