The 21 Best Chelsea Boots For Men in 2023

The Chelsea boot is a staple in everyone’s wardrobe, men or women. You can wear them pretty much year round, depending on your climate, of course. They will elevate your outfits, even if you opt for a more casual look.

What is a Chelsea Boot?

They are a laceless pair of low boots that are meant to be slipped on and off the foot easily. The traditional model comes from two pieces of leather that are called the vamp and the quarters and which meet at the ankle.

They are connected by an elastic that usually sits just under the ankle, and as a general rule they have rounded toes and low heels. There are always exceptions to this rule, and many brands play around with these two pieces to give them an edge.

A Little History of the Chelsea Boot

First designed by J. Sparkes-Hall, Queen Victoria’s cobbler in the 1800s, are a British quintessential footwear style. They were unisex even back then in the Victorian era. But the style really picked up in popularity during the 1960’s, when The Beatles made them part of their unofficial uniform.

Different Types Of Chelsea Boots

Again, as a general rule, Chelsea boots are made of leather or suede, and they come in a rugged street style, or in a more elegant dressy option, if you want to look like some of the best dressed men out there. 

There are so many styles and budgets to choose from, we made a mini guide to help you choose the style that suits your personality and lifestyle the best.

How to Choose your Chelsea Boot

Depending on how you’re planning to wear them, there are some things you should take into consideration when making your purchase.

Material

As mentioned, the two most popular materials Chelsea boots are manufactured from are leather and suede. Leather, especially black leather gives it an uplifted, elegant look, whereas suede is more contemporary. When it comes to leather, there are several subcategories as well. There is the super fine calfskin leather that is more delicate, the more stiffer tanned leather, or even patent leather for a bit of glam.

Suede can also be worn in warmer weather, especially if you opt for a lighter color, but keep in mind that it is not as weather and stain resistant as the leather.

The soles come in either leather, PU or rubber. For weather protection PU and rubber are a better option, but leather looks and feels more sophisticated and it is more comfortable.

Color

Most popular colors are neutral and earthy tones, anywhere from grey to tan, that will go with everything and in any season. Black is more classy, whereas brown is for a more outdoorsy look. And the lighter shades are appropriate for spring or summer.

Ankle Closure

The thing that people notice first when it comes to Chelsea boots are the elasticated U-shaped or vulcanised sides. You will never find Chelsea boots with laces, but most will feature a pull tab at the back of the boot, which makes the boots easier to get on or off.

Heel Height

Most Chelsea boots for men come with about half and inch heels. Some might go a little higher, but usually remain under an inch. The chunky Cuban Style is popular with a certain rock ‘n’ roll vibe, and not everyone can pull it off.

Toe Shape

The completely round toe gives you a very casual look, so if you’re looking for a more formal look, opt for the pointed toe, or at least the one that is a little tapered. Follow this rule of thumb with any footwear and you’ll always look stylish: the more tapered the toe, the dressier the shoe.

Now that you have some basic guidelines to help you get an idea of what to look for, let’s take a look at 21 Chelsea boots that we believe are worth considering.

21. Dr. Martens Graeme II Chelsea boots

Most footwear lists include some type of Dr. Martens boots. They are iconic in their own right with their black and yellow stitching, and this Chelsea boot is great for everyday as well as for more formal outings. If you’re sold to the brand, then it’s a no-brainer. The Goodyear welt, heel pull tab and AirWair rubber soles are details that make this a timeless classic.

20. Blundstone Chelsea Boots

This Tasmanian company is a popular choice in the footwear world, and for good reason. With experience in the business dating back in the 1800s, Blundstone brings you this durable and reliable pair that will survive the worst mother nature will throw your way. Utilitarian with its more rugged look and thicker heels, you will walk comfortably while looking cool.

19. Monochrome Chelsea Sneaker

If you’re looking for a modern approach and comfort in one, consider this sneaker Chelsea boot from Monochrome, a Sydney based premium sneaker brand. Instead of a traditional sole they added a tennis rubber sole, which makes them one of the most comfortable pairs on the market. The Olive green suede also steps outside the box and adds some color to your wardrobe.

18. Astorflex Bitflex Exclusive

These gorgeous handmade booties are made in Northern Italy by a family who’s been in the shoemaking business for six generations. These eco-friendly boots offer you the best market value, and they also look extremely stylish. The toe is the perfect blend of utilitarian and tapered, and the smooth leather will elevate any outfit.

17. Grenson Declan Leather Chelsea Boot

This iconic boot manages to look fresh and in, although it has a very classic design. Portraying a timeless silhouette, they will be a true wardrobe staple for any smart dresser. Exquisitely made from great quality leather, they are adorned with elasticated side gussets.

The heel is woven and it rests on a small stacked heel and leather sole. The almond toe is the detail that makes them stand out from an otherwise classic design.

16. Jack Erwin Ellis Chelsea Boot

Featuring a slip-free rubber sole, these traditional booties from British brand Jack Erwin give you a classy look for a reasonable price. This is one of those shoes you know you can put on and will look stylish without overdoing it, and they will go with literally anything. Great quality full grain calfskin leather and handmade in Portugal, they are a cool addition to any closet.

15. New Republic Sonoma Suede

Those affordable booties from New Republic are accessible, but that doesn’t take away from their style. They come in both suede or leather, and the padded insole and the breathable leather lining add lots of comfort, so you can go on and do whatever you feel like doing. They offer some major bang for your buck, so don’t worry if your budget is slim, they are a great buy.

14. Koio Chelsea Boot

For a great waterproof option, we found this pair from Koio that is a bit higher than the traditional ankle Chelsea boot. Made from oiled suede, they will protect you from even the nastiest weather. The flexible jagged-edge sole is shock absorbent and will provide you with traction, so you can walk for long periods of time and still feel comfortable.

13. Maison Margiela Tabi Chelsea Boot

This split-toe leather bootie from Maison Margiela is a very fashion-forward option for those of you who like to follow the latest trends. Surely not for everyone, you will make a bold statement. They are crafted with the greatest care and with top of the line materials in Italy. You will notice that they carry their signature white stitch at the heel.

12. Alexander McQueen Silver-Cap Chelsea Boots

If you’re looking to make a statement with your Chelsea boots, then you found the right pair in this Alexander McQueen option. If you know the brand, you know they don’t come up with anything traditional and far from boring. The silver Cuban heels speak very loudly and make you feel as if you’re walking on stage every time you put them on.

11. Bottega Veneta Level Chelsea Boots

These bulbous, exaggerated transparent rubber soles that became Danile Lee’s signature style are a mainstay on the fashion house’s footwear collection. Buttery calfskin leather and a slightly sleeker silhouette make these Chelsea boots very current. Many Instagrammers love posing in them, because they look that good! A very trendy take on a traditional model.

10. Arpenteur x Paraboot Elevage Chelsea Boot

These are a great pair of boots for those days when you know you’ll encounter some nasty weather and you need to be prepared. The thick soles and the oiled full-grain nubuck leather will encourage you to face your day confident that you will remain dry. The natural log soles add to your comfort, which make these robust and durable boots a great buy.

9. Common Projects Suede Chelsea Boots

For a refined twist to the classic silhouette, these sand creations from Common Projects are a breath of fresh air. Made from great quality soft suede and with a slightly tapered toe, their rubber crepe soles are in a light shade that give the boot a pleasing aesthetic. The epitome of class, they are perfect for that date night you were looking forward to, or even a more semi-formal affair.

8. Oliver Cabell Chelsea Boots

This brand does not cut corners when it comes to quality of materials and craftsmanship. Made from soft split suede that comes from Venice, Italy, they really didn’t skimp on the materials which give this boot a timeless yet comfortable look. Even the inside of the boot is made from vegetable tanned leather for extra comfort. It comes in a range of earthy shades that are soft and calming.

7. Axel Arigato Chelsea Boots

Style savvy yet extremely comfortable, these boots are great for those long days on your feet. Without compromising on style, the fine grain of the calf leather the boot is made from offers you supreme durability, along with the sturdy rubber soles that are surprisingly flexible. Waterproof and shock absorbing, you can use them literally in any type of weather for long periods of time and your feet will remain happy.

6. R.M. Williams Gardener Whole-Cut Chelsea Boots

This is the perfect boot that is not too dressy and not too casual, which makes it the perfect addition to any wardrobe. With an almond toe and handcrafted from a single piece of leather, these boots are comfortable and durable too. The oil-resistant Goodyear-welted soles provide excellent traction and can be resoled if needed.

5. Church’s Chelsea Boot

For the traditionalists at heart, this one is a true classic black leather Chelsea boot. Made in England by experienced shoemakers since 1873, they feature the pronounced elasticated sides and pull tabs that help you put them on or take them off.

When you picture a classic pair of Chelsea boots, those will probably come as close to that image as possible. Made from great quality leather, you will enjoy them for years and they will never go out of style.

4. M. Gemi The Dritto Suede

A lower version of the traditional Chelsea boot, these beauties from M. Gemi will take your breath away. Although the name says suede they also come in a beautiful leather. Whichever you choose, you will be very happy with this pair of boots made in Italy. Even the lining and the footbed is made from all leather, and the sole is from hand-washed leather. For a touch of luxury that your feet deserve.

3. Saint Laurent Wyatt Chelsea Boots

The Wyatt boot from the renowned designer brand Saint Laurent is a high-end calf leather boot in timeless black. The elasticated gators are the norm, plus the heel is a little higher for a more edgy look.

They are the perfect footwear that add a little glam to your night clubbing with their pointed toes and Cuban heels. For those of you who like to put their stamp on a more classic shoe that can otherwise get a little boring.

2. Saint Crispin’s Plain Boot with Zipper

These boots are anything but plain, and they will bring you an edge with their exquisite craftsmanship and superior design. The textured leather and the inside zippers look very attractive as well as the toe shape, which is a mix between square and tapered.

Handcrafted in Romania, this unique take on a classic Chelsea boot is timeless and uplifts any outfit. Even the sole is made from leather, which adds to your overall comfort.

1. Berluti Caractère Capri Leather Chelsea Boots

If money is no object, then this gorgeous pair of classic Chelsea boots by Berluti is your go-to. The quintessential classic take of the Chelsea is designed to a tee, and the tapered toe design adds a touch of style.

The luscious outer brown Venezia leather along the smooth leather lining and leather soles provide you with superior comfort and a modern design. You will definitely turn heads at your next event when you turn up wearing those beauties.

All these options we looked at are excellent, it’s up to you to decide which suit your budget and your style the best. Have fun shopping!