Fashion & Beauty

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

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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 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

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 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 Chelsea Boot

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 Waterproof Chelsea Boot – Cole Haan Original Grand Waterproof Chelsea Boot

A waterproof Chelsea boot is perfect for the winter months.

The Cole Hann Original Grand waterproof boot is a mix between a boot and sneaker and very stylish. These Chelsea boots have energy foam in the sole for extra cushion for your feet, making them the perfect sneaker upgrade.

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

They give the appearance of a boot but are as light as your average sneaker.

Favorite Trendy Chelsea Boot – Urban Outfitters Dress Chelsea Boot

Urban Outfitters is known for its trendy, cool style clothing so it’s no surprise they have a great Chelsea boot option.

The UO Dress Chelsea Boot is made of suede and a rubber sole.

We love this classic style with an updated toe box. The pointier style of the toe box is slimming and the updated olive suede is super stylish.

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

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 look like a western-style boot, but the elastic gore detail on the sides give 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

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.

Lacy Rhomberg

Lacy Rhomberg

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