A stylish and exceedingly popular boot that was popularised by the Beatles, the Chelsea boot is often regarded as a dressier alternative to Chukka boots. However, they can be challenging to wear properly without appearing out of place.

In this guide, you’ll learn everything that you need to know about Chelsea Boots:

Scroll down to read the entire guide or use the links above to jump ahead!

Beckett Simonon Preston Chelsea Boot On Wall

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Quick Buyer’s Guide

If you just want to buy a pair of quality Chelsea boots, you can use the Quick Buy guide to head directly to the retailers. Otherwise, scroll down to learn more about each pair.

Beckett Simonon

Beckett Simonon Preston Chelsea Boot

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Wolf & Shepherd

Wolf & Shepherd Blitz Chelsea Boot

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Allen Edmonds

Allen Edmonds Liverpool Chelsea Boot

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Carlos Santana

CARLOS by Carlos Santana 1947 Chelsea Boot

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Dr Martens

Dr. Martens Work Fellside Chelsea Boot

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Giorgio Brutini

Giorgio Brutini Aaron Chelsea Boots

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What Are The Best Chelsea Boots For Men?

In this part of the guide, you’ll discover the best Chelsea boots to buy online. We’ll begin with a menu that will help you easily navigate and jump between each listing. Otherwise, scroll down to see them all and read the rest of our guide.

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1. Beckett Simonon Preston [Best Value]

Beckett Simonon Preston Chelsea Boot
  • Color: Black, Bordeaux, Tan, Walnut, Brown
  • Material: Argentinian Calfskin Leather
  • Pricing: $220 [Buy From Beckett Simonon]
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The Prestons are made with a Blake stitch construction from full-grain Argentinian calfskin leather in Beckett Simonon’s Bogota workshop in Colombia. Even without our exclusive 20% discount using our exclusive code “BU20” during checkout, these ethically handmade shoes offer excellent value for money.

Read More: Beckett Simonon Preston Chelsea Boot Review

2. Wolf & Shepherd Blitz [Most Comfortable]

Wolf & Shepherd Blitz Chelsea Boot
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You’ll have never worn boots as lightweight as the Blitz by Wolf & Shepherd. Don’t let the Italian calfskin uppers fool you, these are made with the latest in footwear technology.

From lightweight PhoenixTECH soles to a high-density EVA heel and memory foam footbed, they’re the most comfortable boots that you’ll wear.

3. Allen Edmonds Liverpool [Most Premium]

Allen Edmonds Liverpool Chelsea Boot
  • Color: Black, Brown Suede, Walnut
  • Material: Full-Grain Calfskin
  • Pricing: $370 [Buy From Zappos]
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These classic Chelsea are made in the USA by Allen Edmonds. Featuring the brand’s 360° welt and crafted from full-grain calfskin leather, they certainly offer excellent value for money given the price.

4. Carlos Santana 1947 [Most Stylish]

CARLOS by Carlos Santana 1947 Chelsea Boot
  • Color: Black, Tan
  • Material: Full-Grain Leather
  • Pricing: $300 [Buy From Zappos]
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Named after the legendary guitarist’s year of birth, the 1947 is a beautifully crafted Chelsea boots with rich broguing accents. Made from full-grain leather with a Goodyear welt construction, they’re of impeccable quality and truly stunning to see.

5. Dr Martens Fellside [Chelsea Work Boot]

Dr. Martens Work Fellside Chelsea Boot
  • Colors: Black, Brown
  • Material: Full-Grain Leather
  • Pricing: $140 [Buy Now On Zappos]
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If you’re looking for a rugged and durable Chelsea boot with a steel toe, look no further than Dr Martens. Made for working in hazardous environments, these ASTM approved boots offer slip resistance, a water tight welt construction and a memory foam footbed.

6. Giorgio Brutini Grant [Most Affordable]

Giorgio Brutini Aaron Chelsea Boots
  • Colors: Black, Brown, Tan
  • Material: Leather
  • Pricing: $75 [Buy From Zappos]
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If you’re looking for a cheap pair of Chelseas, the Grants by Giorgio Brutini are a fine choice. Although they won’t offer the same longevity and quality as the pairs listed above, they’ll look the part for long enough to make an impression.

What Are Chelsea Boots?

Top And Side View Of Black Chelsea Boot

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.

Beckett Simonon Preston Chelsea Boot & Box

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.

Perspective View Of Black Chelsea Boot

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

Beckett Simonon Preston Chelsea Boot On StepSeasonally 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:

Men's Chelsea Boot Guide
Reviewed by Theo D., on .
"Thanks for this article, very helpful. Some really nice Chelsea boots recommended here. I think I'll be buying a pair, thank you."
Rating: 5.0 ★★★★★

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