A stylish and exceedingly iconic boot that was popularized 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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What Are Chelsea Boots?

Top And Side View Of Black Chelsea Boot

At their most elemental, Chelsea boots are pull-on ankle boots with a 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 with both suede and smooth leather 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 England during the Victorian era (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, Queen Victoria’s shoemaker, and was intended to serve as riding boots for the Queen.

From that point, they grew to become staple daytime walking boots for both men and women through to the first World War.

Beckett Simonon Preston Chelsea Boot & Box

In the 1960s, 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.

Leather Chelsea Boots: The Iconic Beatle Boot

In the 1960s, Anello & Davide first outfitted the classic Chelsea boot 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 1960s adopted Chelsea leather boots 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.

Such prominent wear by famous figures ultimately cemented the Chelsea as a truly timeless style.

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-1950s. 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 Style Chelsea Boots

The beauty of the Chelsea boot is its versatility. Depending on the color and material, you can wear Chelsea boots with anything from suits to jeans. Truly, they can improve just about any look.

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 classic Chelsea boot will save you precious time and frustration while ensuring you look good.

Are Chelsea Boots Formal?

It depends. The Chelsea boot can be worn with something as casual as regular/skinny jeans & and a classic white t-shirt. Alternatively, they can be dressy enough to be worn with a worsted wool suit.

While it’s technically not the correct thing to do, if you found a black patent leather version that was free of stitching and cut slim, you could even wear them with a tuxedo at black-tie functions. That requires a great deal of savoire faire, though, so tread lightly.

Here are some suggestions as to how to pair Chelsea boots with outfits of different formalities:

  • Casual: Light-toned suede Chelsea boots with bright elastic sides and rubber soles + stonewash jeans.
    • Black suede Chelsea boots + black jeans
  • More Formal: Pebbled leather Chelsea boots with Goodyear welted soles + casual trousers.
  • Decidedly Dressy: Smooth, fine grain leather Chelsea boots (dark brown, burgundy, or black leather) + dress trousers and/or a matching suit.

Paul Anthony The Ensemble Chelsea Boots

Regardless of the setting, it’s important to mind the fit of your pants when wearing Chelsea boots. Jeans or trousers shouldn’t be so long that they cover the entirety of the elastic elements.

In fact, shorter trousers are often better here. Chelsea boots are a classic style statement – don’t be shy in showing them off!

If pairing with dress trousers, try to avoid a break at the cuffs. Jeans can be more forgiving in this regard, especially if you’re going for the “stacked” cuffs look.

Lastly, consider the material and methods used in crafting a particular boot. For instance, a leather sole and Goodyear welt construction paired with a slim, classic silhouette will result in a much more refined pair of Chelsea boots.

On the other hand, take the Dr. Martens featured below. They employ a burly, pebbled leather upper and thick soles that are a trademark of the brand. They’re still Chelsea boots, but they’re much more casual in nature.

The Seasonality Of Chelsea Boots

Beckett Simonon Preston Chelsea Boot On Step

Seasonally speaking, it tends to 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 worn throughout the year as long as it feels comfortable to do so.

If you own a rubber-sole version in pebbled leather, these can function as rain boots in a pinch. Pebbled leather tends to hold up better than regular calf against rain, and a slip-free rubber sole isn’t porous like leather ones.

There are also variations of leather Chelsea boots made with waxed suede uppers that can also withstand wet weather. However, when it’s really coming down, it’s best to opt for duck boots.

Here are seasonally-sound suggestions to get you started:

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

The Best Men’s Chelsea Boots You Can Buy Online

In this part of the guide, you’ll discover the best Chelsea boots for men to buy online. We’ve included examples from varying brands, different levels of craftsmanship, varying price points to demonstrate the flexibility of the Chelsea boot.

1. Beckett Simonon Preston [Best Value]

Beckett Simonon Preston Chelsea Boot
  • Color: Black, Bordeaux, Tan, Walnut, Brown
  • Material: Argentinian Calfskin Leather
  • Pricing: $191* [Buy From Beckett Simonon]

* With “BU20” 20% discount code

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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. Amberjack Chelsea Boots [Most Comfortable]

Amberjack Stylish Chelsea Boots In Smooth Leather
  • Colors & Material
    • Italian Suede: Dune, Midnight, Copper, Grizzly
    • A-Grade Leather: Honey & Cream, Honey, Chestnut, Onyx
  • Pricing: $195 [Buy On Amberjack]
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When they established Amberjack in November of 2020, John Peters and his team of industry experts set out to create shoes designed for the future of work. To achieve this, they paired advanced materials with modern design and sustainable production.

The Chelsea, their most recent release, embodies the smart-casual attire that is rapidly proliferating around the world. With rounded toes, a heat-activated foam midsole, breathable leather lining, and premium leather uppers, they’ve put forth an extremely stylish and comfy pair of Chelsea boots.

3. Allen Edmonds Liverpool [Classic Chelsea Boots]

Allen Edmonds Liverpool [Classic Chelsea Boots]
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Allen Edmonds is widely recognized for creating classic shoe styles that are handcrafted in the USA; the Liverpool Chelsea boots only help to solidify their long-standing reputation.

The materials employed are absolutely top-of-the-line; European calfskin, Vegetable-tanned leather soles with rubber elements, cork insoles, and a leather lining. Likewise, their classic silhouette is exceptional thanks to an integrated pull tab, almond toe, and polished uppers.

When it comes to a superior pair of Chelsea boots for men, you can’t go wrong with AE.

4. CARLOS by Carlos Santana Mantra [Brogue Chelsea Boots]

Carlos by Carlos Santana Mantra Chelsea Boot
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The Mantra Chelsea boots by Carlos Santana demonstrate how broguing elements should not be reserved solely for traditional quality footwear. Indeed, they impart attractive details to the Mantra.

The look of the Mantra is also augmented by red accents, both in the elastic gore and the sole, that beautifully pair with the Cognac Calfskin upper.

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-reinforced rounded 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.

The chunky, waterproof rubber soles, yellow stitching, and yellow accent tabs are a trademark Dr. Martens, though they also serve to make these comfortable boots adequate for all types of hard work.

Black leather is also available, though these pebbled brown boots are extremely popular for good reason.

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. There’s no doubt that you can find a great pair of Chelsea boots that match your personality and preferences.

Moreover, 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 over many years.

What Next?

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

"Thanks for this article, very helpful. Some really nice Chelsea boots recommended here. I think I'll be buying a pair, thank you."
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