Even though Chelsea boots have existed since the 19th century, the best Chelsea boots are still a staple part of fashion in men's fashion thanks to their simple but enduring style. They are even more popular for their versatility. They can be paired with many looks ranging from a casual, official look of a blazer and tailored trousers to casual weekend wear with a statement t-shirt or rugged denim.

A classic Chelsea boot can claim both rock n roll and a regal heritage, and they were invented with Queen Victoria's shoemaker. They were initially known as paddock boots intended for horse riding and walking. J. Sparkes-Hall made the first Chelsea boot for Queen Victoria because she wanted shoes that didn't have laces to wear the shoe while riding because laces were often caught up in her stirrups.

The Chelsea boot styles are worn by trendsetters, but they are also a perfect way to demonstrate your unique personality with quality craftsmanship and keen attention to detail. However, finding the best pair of Chelsea boots can be a daunting process, and therefore, we have listed the best Chelsea boots to keep your feet comfortable and, at the same time, step up your style. We have also compiled a detailed buying guide that will help you navigate the buying process easier.

1. Bruno Marc Men's Suede Leather Chelsea Boots

Bruno Marc Men's Urban-06 Black Suede Leather Chelsea Ankle Boots - 6.5 M US
  • Runs a bit large, order a 1/2 size down. Premium...
  • Stretch bands with good elasticity and pull up tab...
  • Well-made leather lining keeps your feet warm and...
  • Soft EVA foam footbed keep your feet fresh and...
  • Durable TPR outsole provides good traction and...

Bruno Marc Chelsea's brown suede leather boots are one of the most affordable pairs of Chelsea boots, and they are a top choice as apart from the pricing, they make a good stylish footwear choice all week. Despite the low price, this pair is made with suede leather that is very similar to high-end models and also has a uniquely crafted leather lining that will keep your feet warm in the cold seasons.

Bruno Marc suede Chelsea boots have good elasticity and a pull tab that makes them easy to slip on and off, and you will not see the need for laces ever again. The pair of boots also feature an EVA foam footbed that keeps you comfortable on your feet all day and also has a slip-resistant TPR outsole that gives maximum traction and is tear-resistant. Even though these brown Suede boots lack the Blake or Goodyear welt, they will last you a long while before you need to replace them.

  • Pros
  • Affordable Chelsea boot
  • EVA foam footbed
  • Leather lining
  • Tear and water-resistant
  • Available in many colors to fit any style
  • Provides maximum traction thanks to the sole
  • Friendly for wide feet
  • Rubber sole
  • Cons
  • The Chelsea boot lacks the Blake or Goodyear welt.

2. Dr. Martens Men's 2976 Chelsea Boot

Dr. Martens Men's 2976 Chelsea Boot
  • Leather: Cowhide
  • Textured elastic
  • Slip-on style
  • Chelsea boots

Dr. Martens Chelsea boots for men were made by Dr. Martens in the 1970s, and they have lived up to date thanks to their quality build and the fact that they can be dressed stylishly. The high-end footwear features a sturdy matte leather upper and a patented AirWair rubber soles that guarantee non-slip and comfortable traction. These Chelsea boots also feature a Goodyear Welt construction meaning the quality upper and the sole are heat-sealed, and Z-welt stitched to guarantee maximum longevity.

The Chelsea boots are made with an easy elastic ankle and a pull tab with an iconic logo that ensures you can wear them within a few seconds and the classic Chelsea boot is available in a few colors. However, remember to size down as Martens shoes usually run on the large side, but the classic silhouette shoe can also be worn by women thanks to a unisex design.

  • Pros
  • Abrasion and slip-resistant pair of shoes
  • Patented AirWair rubber soles
  • Slip-on Chelsea boot design
  • Air-cushioned sole
  • Pull tab and an elastic ankle
  • Durable leather upper
  • Cons
  • This Chelsea boot can be uncomfortable and stiff to break in.

3. R.M. Williams Men's Comfort RM Leather Chelsea Boots

R.M. William's black leather Chelsea boot is the best leather pair, and these shoes have been made from black cow leather, and the brand has made a name for itself for being the master producer of leather boots. These R.M. Williams stylish shoes are made in Australia and have been handmade with a single piece of leather and stitched at the back, meaning the black Chelsea boots are very comfortable and durable. Without seams, no water can get into your footwear. The R.M. Williams silky-smooth leather molds to your feet's shape and gives you a figure-hugging comfort, and it also has a block heel that will offer an extra lift that will keep you comfortable during your day.

R.M. Williams black Chelsea boots also use a Goodyear welt that offers maximum durability and waterproof capabilities, allowing them to get soled again, which is not a requirement. These boots can be worn with a pair of straight-leg jeans, a bomber jacket, or a brown trench coat.

  • Pros
  • Molds the feet's shape
  • Goodyear welt offering maximum durability
  • Slip-on footwear
  • It can easily be paired with jeans or a suit
  • Versatile style
  • High-quality handmade shoe
  • Distinct 2-tab cuff.
  • Cons
  • Some sizes are too narrow for wide feet

4. Saint Laurent Wyatt Chelsea Boot

Saint Laurent is a luxury brand that has made a name for itself on the back of Hedi Slimane era rock ‘n’ roll aesthetic and produces the best Chelsea boots in the market today. The Wyatt style boots from the Saint Laurent brand are a classic boot shape made in Italy and from black calf leather and have elasticated gators that are a key in almost all Chelsea boots. They are a suitable pair for anyone looking for a high-end pair, and the brand reinvests the Wyatt boot each season.

Saint Chelsea boots feature a Cuban heel that adds height and drama to your style and is available in various fabrics and colors, and they can be dressed either up or down. This Made-in Italy footwear also has an ankle-hugging elastic, a smartly designed pull tab hidden inside the shoe's back to get the footwear on and off easily, and an almond-toe silhouette. Also, because they are a luxury pair and have unique features that you will not find in other boots, they come at a high price.

  • Pros
  • Made in Italy
  • Made from durable calfskin leather
  • Hidden pull tab
  • Ankle hugging elastic
  • Available in different colors
  • Almond-toe silhouette
  • Cons
  • Highly-priced

5. Chelsea Slip-on Suede Boots For Men by Cestfini

Camel Chelsea Boots Men Classic Elastic Dress Boots Casual Men's Suede Chelsea Ankle Boots
  • GOOD FIT - These mens boots are using standard...
  • PREMIUM UPPER - The mens chelsea boots upper is...
  • COMFORT INSOLE - The softer insole of mens dress...
  • NON-SLIP SOLE - Men's chukka boots with a...
  • CLASSIC DESIGN - Classic and elegant design is...

Chelsea Slip-on Suede Boots are designed with a comfortable tapered toe and a high cushioned crepe rubber outsole with a unique brand signature heel-stamped gold lettering. These boots are ideal for the edgy hopping man and the elegant-suited man, meaning it is a suitable everyday wear option for men of all fashions and styles. 

The cushioned stationary insole and stacked wood-grain heel  soles come in a similar shade to the boots to give you a seamless aesthetic experience, and with Italian craftsmanship, you are guaranteed maximum durability. These boots are also versatile as they are available in different suede colors .

  • Pros
  • The Common Projects footwear includes a dust bag
  • These shoes have pull tabs and elasticated sides
  • Suede lining
  • Gold-stamped serial numbers
  • Versatile boots
  • Cons
  • The suede boots are not waterproof

Factors to Consider Before Purchasing the Best Chelsea Boots

1. Material

When it comes to the best Chelsea boots, most of them are made from different materials, including:

a). Top Grain

This type of leather is used on the top exterior of the cowhide, and it is sanded and buffed to get rid of any surface imperfections, which in time develops to form a nice patina. The top grain is premium-grade leather, and the nubuck leather is another type of top-grain leather.

b). Full-Grain

The leather type is made from the cross-section of the hide, and it's thicker and more durable. However, it takes longer to break in with this leather type, and the Chelsea boot may feel stiff, but just like the top grain leather, it develops a nice patina.

c). Calf Leather or Calfskin

This leather type is sourced from young cattle and has a delicate and velvet-like texture. It is mostly used by premium brands because of its quality and will develop a nice patina.

d). Genuine Leather

This leather type relies on different hide parts, and they are bound together by glue. The Chelsea boot's leather type is prone to tearing and stretching, and it is quite affordable for a Chelsea boot that's meant to be worn for a few seasons.

e). Suede

The suede leather type is sourced from the hide's underside, and it's not that durable and needs special cleaning. Also, suede material in the footwear will last you only a few years.

2. Ankle Closure

Chelsea boots usually feature two types of different closures, and they include:

a). Elastic/ Slip-on

This is the most common type of closure, and it allows a better motion range when it comes to ankle mobility and walking while the boot is still being secured to your feet. It is the most versatile and traditional closure.

b). Zippered

When it comes to Chelsea boots, zippers are not as common as you would find in mid-calf boots, but the pairs of Chelsea boots with zippers usually feel more secure on the feet. Notably, zippers should be clean accordingly as debris and dirt may cause the zipper to jam.

Additionally, the best Chelsea boots usually come with a pull tab at the back that makes wearing the boots and getting them off quicker.

3. Heel Height

Most Chelsea boots usually come with a short heel similar to the one in a work boot, and with the heel being a fraction of an inch, it's not noticeable. However, other Chelsea boots feature a Cuban heel raised to about 1.5 inches and will give you a taller appearance, and the heel is mostly found in cowboy boots with a slightly tapered cut. This heel style was popularized by the famous Beatles, and it offers a rock n roll mood.

4. Color

Chelsea boots for men usually come in different neutral colors unless you are looking to wear the Chelsea boots for a specific look. These neutral colors offer more versatility, and men can wear and style Chelsea boots with plenty of pieces in their wardrobe.

The best colors for men's Chelsea boots would be organic and earthy shades, including greys and browns and traditional black. The brown colors may feel more rugged and outdoorsy than the black leather Chelsea boots, which come in an urban style, whereas light-colored shoe is suitable for casual summer fashion.

5. Welt / Repair

To get the best value out of your Chelsea footwear, opt for a pair of Chelsea boots that feature a Blake or Goodyear stitch, and these welts are easily replaceable by your local cobbler. These welts are very important, especially if you purchase full-grain leather Chelsea boots that will last you for several years. The stick-on and cemented soles are usually glued together, and this makes them unrepairable, and so, if the company does not disclose the type of stitching, you should assume they are cemented.

6. Size

Sizing varies from brand to brand, and more often than not, Chelsea boots usually run almost a size larger, so it's important to size down accordingly. However, before making your footwear purchase, read the fit information that has been provided by the company because the boot fit matters since a Chelsea boot does not come with laces.

7. Toe Shape

The men's Chelsea boots suited for smart-casual occasions are tapered and feature an end in a point that feels more formal and could even be paired with a suit. On the other hand, the rounded toes are usually casual but check to ensure that your Chelsea boot is not too bulbous, but a bit of tapering gives more elegant and flattering vibes.

8. Style

Men's Chelsea boots can be styled differently because they are very versatile, but it should come down to the individual fashion sense. However, some general tips would be to choose leather Chelsea boots for formal occasions and the suede Chelsea boots for a more casual and relaxed look. You can also rock your Chelsea boots with jeans and ditch the sneakers for weekends and pair them with a classic white t-shirt or denim or checked overshirt.

Black Chelsea boots are shoes that will match well with black jeans and a black turtleneck, and the black boot style can also go well with a brown suit or grey and black shades.

Frequently Asked Questions on the Best Chelsea Boot

1. Why are leather Chelsea boots for men so popular?

These Chelsea boots for men are popular because they transcend the fashion trends and don't go out of fashion since their invention. On top of the Chelsea boot being a popular fashion choice, the footwear is common because of how durable and comfortable it is.

2. What kind of pants go with Chelsea boots?

Chelsea boots are very versatile, and therefore, they can be worn with a variety of pants, including chinos, jeans, slim-cut suits, and other tapered varieties.

About the Author Brian

Hello, I'm Cindy. I’m a super duper mega hiking enthusiast, with a love for everything that has to do with outdoors, hiking, gear, footwear and more.

Share your thoughts

Your email address will not be published. Required fields are marked

{"email":"Email address invalid","url":"Website address invalid","required":"Required field missing"}