Our 6 Favorite Men's Chelsea Boots [And How to Rock Them]

September 29, 2021
by Christine Devereaux
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We are here to introduce you to the Chelsea boot, the go-to shoe of choice for style-minded men the last couple of years.

Chelsea boots reign supreme because of their versatility - dressier than a sneaker, cooler than a dress shoe, and a slip-on style that is perfect for guys on the go.

The Chelsea boot goes way back. But, the name came about in the 1950s in London’s Chelsea neighborhood.

You’ve seen Chelsea boots on high-brow royalty and grunge rock ‘n’ roll stars over the years. There’s a reason these boots are worn in a wide range of circles. And we believe this trend is here to stay for a while.

Here are our 6 favorite men’s Chelsea boots this season.

What is a Chelsea Boot and How to Wear Them

Chelsea boots are a fashion-forward upgrade from your traditional sneaker, but you need to know how to wear them.

First and foremost, a Chelsea boot has two key components.

Chelsea boots hit around the ankle and they are traditionally made up of two distinct pieces of leather. The leather can be fastened together in many different ways, but the main distinguishing mark of a Chelsea boot is the toe.

The Chelsea boot toe is rounded.

This allows you to dress them up or down, giving them the ultimate versatility. In general, a more pointed toe is indicative of a dressier shoe. A more rounded out toe allows you to wear your Chelsea boots in place of sneakers and dress shoes.

Chelsea boots can set you back a few hundred dollars or a few thousand dollars, but what’s most important is finding a pair that is comfortable and have the everyday wear look.

A nice pair of Chelsea boots can put your whole outfit together. Whether you are running errands around town or going out to dinner and then a show at the theater, Chelsea boots are a great option.

The nice thing about a nice quality pair of leather Chelsea boots is the older and more worn they are the more distinguish they look. That cannot be said about most items in your closet.

Favorite Classic Chelsea Boot - Clarkdale Gobi Classic Chelsea Boot

Clarkdale Gobi Classic Chelsea Boot

A black leather Chelsea boot is a good place to start if you are new to the style.

Clarks is a brand we know and trust because of its functionality and durability. The Clarkdale Gobi is no exception.

It’s the perfect mix of classic and trendy and will go with literally any outfit you wear.

This is also the Chelsea boot that you can commute to work in every day or walk around Europe for a week on vacation without worrying about blisters or sore feet.

Favorite Splurge-Worthy Chelsea Boot - Saint Laurent Joey Chelsea Boot in Suede

Saint Laurent Joey Chelsea Boot in Suede

From the direction of fashion designer Anthony Vaccarello, the Saint Laurent Chelsea boot is made with Italian leather and as durable as they come.

We know this boot is pricey than the rest of the boots on here, but it’s definitely worth the splurge.

The high-end leather is durable, yet walkable, which is a crucial factor. The pliable calfskin leather in this Chelsea boot allows for all day and nightwear.

There is a tiny heel on this Chelsea boot, but it doesn’t disrupt the comfortability.

This is a great boot to transition from work to a cocktail event without having to stop home and change into dress shoes.

Favorite Eco-Friendly Chelsea Boot - Nisolo All Weather Javier Chelsea Boot

Nisolo All Weather Javier Chelsea Boot

Chelsea boots are just better when they give back.

The Nisolo All Weather Chelsea Boot is made with a thin yet durable material for a sleek, put-together look. Plus, they are water-resistant, so you won't have to worry about a little rain here or there.

But if the style and durability of these boots don't get your attention, their sustainable & give-back practices will. Everyone behind the boot is paid a fair, living wage. (Unfortunately, that's not the norm in the fashion industry).

Wear these boots with jeans and a puffy vest, or with your dress pants while you are commuting to work.

Favorite Trendy Chelsea Boot - Jack Erwin Ollie Chelsea Boot

Jack Erwin Ollie Chelsea Boot

Jack Erwin is known for its trendy, cool style shoes so it’s no surprise they have a stellar Chelsea boot.

The Jack Erwin Ollie Boot is made of suede and a lug sole for comfort that can keep up with your jaunts around the city.

These Chelsea boots would look great with a bomber jacket and hip sunnies for day drinking at a local brewery or cocktail bar.

Favorite Western Chelsea Boot - Frye Grady Chelsea Boot

Frye Grady Chelsea Boot

The Frye Grady is our favorite western-style Chelsea boot.

They’re the perfect mix of Chelsea and cowboy and with a brand like Frye, you will probably be able to pass these boots down to your grandkids if you take care of them properly.

The detailing on the front as well as the heel looks like a western-style boot, but the elastic gore detail on the sides gives it the ease and function of the Chelsea boot.

While more of an investment boot, Frye boots are great quality and will last you for years. You can dress these Chelsea boots up or down depending on the occasion and they are much classier than traditional cowboy boots.

Favorite Budget Chelsea Boot - H&M Chelsea Boots

H&M Chelsea Boots

If you aren’t quite ready to spend hundreds of dollars on a Chelsea boot, we have a budget option for you.

H&M makes a Chelsea style boot that is quite fashion-forward. These boots are $50 and made of polyester, so they won’t last forever, but the price point is great if you are looking for a fashion-forward option and trying to stick to a budget.

They are super easy to slip on and off and are a great upgrade from your everyday Vans.

Whether you are a style-conscious guy or just looking to upgrade your footwear this winter, the Chelsea boot is a great versatile option to wear both casually or dressed up.

After you purchase your new Chelsea boots, you might be interested in learning how to break them in properly so you can get maximum wear with minimal blisters.

Our Favorite Men's Chelsea Boots:

  1. Favorite Classic Chelsea Boot Clarkdale Gobi Classic Chelsea Boot
  2. Favorite Splurge-Worthy Chelsea Boot Saint Laurent Joey Chelsea Boot in Suede
  3. Our Favorite Eco-Friendly Chelsea Boot-Nisolo All Weather Javier Chelsea Boot
  4. Favorite Trendy Chelsea Boot - Jack Erwin Ollie Chelsea Boot
  5. Favorite Western Chelsea Boot - Frye Grady Chelsea Boot
  6. Favorite Budget Chelsea Boot - H&M Chelsea Boots
About the Author
Christine Devereaux is a style and gear junkie. She loves the outdoors and picking out clothing and home goods for her husband, son and dog.

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