Mens Chelsea Boots- Complete Guide to Buy and Style

Chelsea boots have been gaining in popularity the past couple years because of their versatility, and minimalist style. You’ve might have seen them featured on GQ’s “must have” or worn by style icons like The Beatles, David Beckham, Kanye West, Harry Styles, Lenny Kravitz and many more.

The fact that you can wear these with ripped jeans as well as a suit makes them a staple in every man’s closet. In this article, I will be going a brief history of the Chelsea boot, different types of Chelsea boots, how to style them, and how to find the perfect pair for any budget.

The History

The Chelsea boot dates all the way back to the mid 18th
Century by a man named J. Sparkes-Hall. These boots were created for Queen Victoria. Queen Victoria was looking for a slip-on boot so the laces would not get stuck in her stirrups while riding horses. Originally named the “Paddock Boot” and were meant for riding. After the creation of vulcanized rubber (elastic on the side of the boots) invented by Charles Goodyear in 1830 it made the boots easier to slip on and off.

It wasn’t until the 1950’s they earned the name Chelsea boots becoming a popular in the UK among artist and musicians in Western London’s Chelsea’s neighborhood. Worn by up and coming rockers The Rolling Stones and the Beatles they started to be referred to as the “Chelsea” boot.

Types of Chelsea Boots

There are many types of Chelsea boots depending on construction, material used, and shape. The majority of Chelsea boots are made out of suede or leather and have a leather or crepe sole. Some types of boots have Cuban or “stacked” heel.

Leather Chelsea Boots

Leather Chelsea boots are both formal and informal and you can dress them up or down. You can find formal types like sleek Italian Chelsea boots to go with a suit or sport coat. Also, more casual versions like Australian work boots with a rubber or crepe sole.

Suede Chelsea Boots

Suede Chelsea boots are the most popular right now (in my opinion) because of their versatility. You can dress these up with a nice shirt or sweater or wear them with some ripped blue jeans and a white tee shirt. These come in all types of variations and colors.

Crepe Sole

The term “crepe” is referring to the material that the sole is made out of. It is made from coagulated latex that is rolled out in crinkled sheets. This rubber is usually tan or black and has a rough spongy texture. It is made from usually a more casual but more comfortable boot made popular by Common Projects.

Leather Sole

Chelsea boots that come with a leather sole and stacked heel are usually higher quality and more formal. High quality leather soles if constructed properly will mold to your feet over time very comfortable.

How to Style

Chelsea boots can be worn in many ways, that is why they are becoming so popular. If your style is more rugged and casual meaning tees, ripped, jeans, and the occasional biker jacket I would suggest suede. If you tend to have a more formal polished wardrobe think blue suits, crisp white oxford shirts, cashmere sweaters, I would suggest a nice leather pair. Regardless of your style I will go over 3 popular ways to style Chelsea boots.


Wear a pair of medium to light brown suede Chelsea boots with some faded or distressed blue jeans and a crisp white tee shirt. It is made from the perfect combination of style and versatility for your fit rotation. Put a sweatshirt over the tee for some more layering or dress it up a bit with a flannel.

Night out

Everyone has those nights where they are feeling themselves. You are meeting a date or going to a suave club and want to look like a rock star. For this fit you can pair black leather or medium brown suede Chelsea boots with some skinny black jeans and your favorite black leather biker jacket.

Nine to Five

Do you ever have to go from the office straight to a happy hour or party? This is your look. Match an impeccably tailored blue suit and white button-down shirt with a pair of medium to dark brown Chelsea boots. Then after work keep the jacket and change into a pair of crisp dark blue jeans and a clean white tee and you’re ready to hit the town.

How to Buy

There are many types and price ranges depending on the style, material, brand name, and craftsmanship you are looking for. Below are some of my favorites both inexpensive and expensive.


Here are some very good quality Chelsea boots for under the $200 price point. These include both leather, and suede. The first are a company called Shoe the Bear. They make boots and tennis shoes of quality at an amazing price point. The “Dev” boot is a perfect suede boot that comes in different shades of brown suede as well as black. This boot is constructed with a leather sole and wood heel at a price point of $160. Shoe the bear also has a nice leather pair named the “Arnie” that comes in a smooth black color and a beautiful medium brown at a price point of $170. If you are looking for something a little more casual and easier to break in the New Republic “Chuck” boot is the perfect combination at a great price point of $99. All of these boots will not break your wallet or your feet.


If you enjoy the finer things in life or just have a $1000 burning a hole in your pocket then these are the right boots for you. These are top of line in style, materials, and craftsmanship… that being said they come at a price. Saint Laurent is known for their classic yet edgy boots. The Wyatt comes in multiple different suede colors as well a smooth leather and is the one you will see on most celebrities with a price point of $945. If you’re a little more daring you can go for the Wyatt Harness boot that has double chain harness strap and stacked heel. These will set you back $1,145 but will definitely turn some heads. The last pair is another classic mentioned above the Common Projects crepe sole boot. These are the perfect combination of quality materials, sleek look, and comfort for a price point of $530.

Whether you’re headed to the office, club, or grocery store Chelsea boots should be a staple in every man’s closet. There are many types of Chelsea boots to choose from, when picking out the perfect boot craft around you own wardrobe and style. Be conscious of the material and quality used and align that to your price point. When you purchase your first pair of Chelsea boots you are one piece closer to crafting the perfect wardrobe.