The Ultimate Guide To Chelsea Boots: Best Boots, Style History & How To Wear

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What Are Chelsea Boots?

At their most elemental, chelsea boots are ankle-height pull-on boots with stretchy elastic material (sometimes referred to as “gore”) on both ankles. They have no fastening mechanisms such as laces or buckles. They most closely resemble jodhpurs, just without the leather strap and buckle.

They’re made in various leathers and suedes in a multitude of colors. While they’re often unadorned, there are plenty that are available with medallions, broguing, cap-toe details, and more. The main point is that they’re ankle-height and made to be pulled on and nothing more.

This boot is one of the smartest investments a man can make in his wardrobe, assuming he lives in a place that experiences cold weather for at least a few months out of the year. Able to be dressed up or down, it’s smart to spend good money on a versatile pair that can be resoled many times over.

Chelsea Boot History

Like so many articles of clothing we wear in modern times, the chelsea boot has roots in Victorian England (which, for you history nerds, lasted from 1837 until Queen Victoria’s death in early 1901).

The first version was created by J. Sparks-Hall, bootmaker to Queen Victoria. They were a daytime walking boot that was a staple for both men and women through the first World War.

In the 1960’s, as mod culture became prevalent in London, it was common to see men in slim suits wearing chelsea boots on their scooters. This drew heavily on Continental sartorial influences, which were predominantly French and Italian. If you think about how many images of suited Italian men on Vespas you’ve seen in your life, you’ll see that this is clearly taken from the Mediterranean.

This was at a time when the European continent was finally healing after the bloodiest war in its history.

Beatle Boots

In the 1960’s, Anello & Davide first outfitted the chelsea with a Cuban heel, which more closely resembles a cowboy boot heel than a men’s dress heel. In 1961, a couple of obscure Liverpudlians you’ve probably never heard of named John Lennon and Paul McCartney were inspired by chelsea boots in Anello & Davide’s shop window.

They ended up ordering four pairs, the other two being for George Harrison and Ringo Starr, their equally little-known bandmates. The boots, in conjunction with Nehru-collar suits, became the group’s signature look, a far cry from the leather jackets and jeans they donned while cutting their teeth in German clubs.

Though they were made famous by The Beatles, many rock bands from the 1960’s adopted the chelsea boot into their wardrobes. The Rolling Stones wore them. The Beach Boys wore them. The Yardbirds wore them. The Kinks wore them. The list goes on.

Where Does The Term “Chelsea” Come From?

The King’s Road area of West London is in the (ahem) Chelsea neighborhood, so you can see where we’re going with this. The neighborhood was a gathering place for artists, filmmakers, and other such intellectuals in the mid-1950’s. Named the “Chelsea set” by the media, they often wore this style of boot and soon the name became synonymous with the footwear.

How To Wear Chelsea Boots

The beauty of the chelsea boot is its versatility. Depending on the color and material, they can be worn with anything from suits to jeans. This versatility, combined with the ease of getting them on and off, makes chelsea boots an excellent option as a travel shoe. Getting through airport security as quickly as possible is the goal of any air traveler, and the chelsea boot will save you precious time and frustration while ensuring you look good.

Formality

The chelsea boot can be worn with something as casual as jeans or as dressy as a worsted wool suit. While it’s technically not a correct thing to do, if you found a black patent leather version that was free of stitching and cut slim, you could wear it with a tuxedo. That requires a great deal of savoire faire, though, so tread lightly.

Here are some suggestions as to how to pair this boot with various outfits:

• Suede chelsea with bright-colored elastic sides, pebbled leather chelseas: jeans, casual trousers
• Smooth calfskin in black, brown, or burgundy: Dress trousers & suits

Seasonality

Seasonally speaking, it tends to usually make sense to wear Chelseas (or any type of boot, for that matter) during autumn and winter. Nevertheless, there are exceptions like the desert and Chukka boot. Consequently, the Chelsea boot is quite versatile and can be warm throughout the year as long as it feels comfortable to do so.

If you own a rubber soled version in pebbled leather, these can function as rain boots in a pinch, as pebbled leather tends to hold up better than regular calf against rain, and rubber soles aren’t porous like leather ones. Still, it’s best to own duck boots for this purpose.

Here are some suggestions to get you started:

• Spring: Brown or tan smooth and full-grain or suede in shades of brown.
• Summer: Light shades of tan in smooth or suede leather.
• Autumn: Suede in various shades of brown,
• Winter: Black, brown, or burgundy leather, smooth or pebbled

Closing Thoughts

As we’ve previously stated, the chelsea boot is one of the most functional, versatile shoes a man can have in his rotation. If you live in a temperate or cold climate, it should definitely be one of the first five pairs of shoes that you own. Wearable with anything from jeans to suits, it makes sense to budget for a really well-made pair that can be resoled over and over again so as to maximize your investment.

What Next?

Now that you have learned about Chelsea boots, check out some our related footwear guides for men:

• Jodhpur Boot Style Guide
• Chukka Boot Shoe Guide
• Best Dress Shoes For Men
• Most Comfortable Shoes For Men
• Men’s Shoes Homepage