Skip to main content

Your Cart

Close Alternative Icon
The Best Men’s Chelsea Boots of 2020 The Best Men’s Chelsea Boots of 2020

The Best Men’s Chelsea Boots of 2020

Chelsea boots are one of the most iconic and versatile boot styles in the world - this is thanks to their completely unique elastic goring. These stretchy panels at the ankles of the boot make the boot easy to take on and off without the need for laces, while also giving the boots a highly distinctive design pattern.


If you want to know how to wear Chelsea boots, it helps to start with a little history. With the invention of vulcanized rubber in the 19th century, elasticized panels that wove textiles with rubber became an exciting new alternative to the traditional alternative of laces or buttons. It was Queen Victoria’s royal bootmaker, J. Sparkes-Hall, who is credited with first applying this invention to footwear. For the second half of the 19th century, these “elastic ankle boots” were a relatively popular style for men and women alike and initially served a mostly functional purpose.

Chelsea boots earned their current name during the 1960’s, when this style came back into fashion around the West London neighborhood of the same name. Iconic adopters like the Beatles, the Rolling Stones, and Jimi Hendrix brought revived credibility to the design and the new name stuck. This was also the era when Chelsea boots became high fashion for the masses.

Design Details

Quality Chelsea boots are simple in appearance, but relatively difficult to make versus other boot designs. This is first because the clean vamp of the boot requires a large, single piece of leather, which requires a high-quality cutting criteria. The shaping of the vamp also requires some skill, as the leather needs to be “tamed” in order to fit the natural shape of the foot’s instep. Finally, any kind of recraftable construction, like Goodyear welt construction will extend the longevity of your boots. These kinds of details separate quality craftsmanship from the rest.

The shape of the elastic cutout varies by style and is mostly an aesthetic choice, but the materials for the upper and outsole greatly change the look of the boot. Leather outsoles tend to be a bit more formal and streamlined, while rubber outsoles are a bit better for inclement weather and more comfortable for everyday wear. Full grain leathers create a polished, dressy look, while oiled suede brings a little more texture and warmth. Waxed suede is a particularly desirable material, since the boots naturally burnish as the boots are worn, making them look better over time.

How to Wear Chelsea Boots for Men

If the occasion is formal, nothing pairs quite as nicely as a pair of Black Cavalier Chelsea Boots and a suit. This clean, crisp look is all about understated sophistication.

The Best Men's Chelsea Boots: The Cavalier

For a more functional, no-nonsense look, a rubber outsole with thick leather like the Brown Duke is a great accompaniment to stormy weather. These also work with nearly all types of denim and will showcase a lot of character as the leather breaks in over time.

The Best Men's Chelsea Boots: The Brown Leather Duke

If you want more of a rock-and-roll inspiration, look for leathers that will show more distinct wear patterns over time. Waxed suedes like the Dark Olive Suede Duke will burnish over time, making them perfect to pair with dark slacks or ripped jeans.

The Best Men's Chelsea Boots: The Dark Olive Suede Duke

The Best Chelsea Boot for the Modern Man: The Cavalier Shadow Grey Suede

Key Features: Shadow Grey WeatherSafe™ Suede Poron® Antimicrobial Shock Absorbing Insole, Leather Outsole with TPU Studs for Traction

Why we love it: A sleek take on a class silhouette, this dress Chelsea looks right at home with a suit, but can still be worn with a pair of jeans. It’s stylish, but never stuffy, and ours are built with the materials to stay in form for years to come.

What others say: “Their take on the Chelsea boot is perfectly understated and well made.” - Men’s Journal

Also available in: Black, Dark Brown Suede, and Sequoia.

Shop Now

The Best Casual Chelsea Boot: The Duke Honey Suede

Key Features: Honey WeatherSafe™ Suede, Poron® Antimicrobial Shock Absorbing Insole, DuraEVA™ Comfort Strip, Durable Studded Rubber Outsoles

Why we love it: This is a classic Chelsea boot that elevates your daily wardrobe to keep you looking cool and relaxed, no matter what you pair with it. Easy to dress up or down, this boot is as versatile as the man who wears it.

What others say: “Thursday Boot Company has found a perfect balance of high quality materials and reasonable cost.” - Mark W.

Also available in: Black, Brown, and Dark Olive Suede.

Shop Now

"The Most Versatile Boots"

Chelsea boots have grown enormously popular, and it’s not hard to see why. Their unique design, high comfort, and extreme versatility make them an excellent complement to almost anyone’s wardrobe. For whatever long and winding roads you may encounter, there’s nothing quite like a pair of Chelsea boots to help you on your journey.

Learn More from Thursday

Have A Question?

No problem! We're always here to help. Just click below for assistance.