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Men’s Chelsea boots have galloped their way into the daily outfits of stylish guys over the better part of a decade. In that time, the pull-on style has both sustained its value as a boot to dress up and has arguably increased in popularity as a casual take on the work boot. And while it was originally invented in the 1830s as a laceless equestrian boot for Queen Victoria, the best Chelsea boots rose to fame in the US from an entirely different source — music.
Formerly known as the “Paddock” boot, The British Invasion of the 1960s didn’t just bring groovy music to the US — it also brought a whole lot of style. From psychedelic color blocking and monochromatic fits to big sunglasses and even bigger hair, the music scene of the time impacted the way Americans dress so severely that pieces of it are still found everywhere, some 60 years later. While society left the lacy cravat back in time, the Chelsea boot hit harder than the release of “A Hard Day’s Night.”
While this was happening, the Australian-based Blundstone had taken the original concept of the Paddock boot and turned it into a work boot that would define the brand forever — the now-legendary Original 500 Boot.
The men’s Chelsea boots of today don’t look a thing like Queen Victoria’s but are very similar to those rocked in the ’60s by bands like The Beatles. They’re immediately recognizable by their elastic goring in the middle of the shaft that allows them to go on so easily. Hundreds of brands have put their own spin on this classic, refining the pull tab, messing around with different leathers, and even adding sneaker soles. But one thing that remains the same is that the best Chelsea boots are convenient, comfortable, and, in a modern way, shagadelic.
BEST MEN'S CHELSEA BOOTS
Thursday Boot Co. Duke Chelsea Boots
Thursday Boot Co. is a direct-to-consumer brand that has fully engrained itself in conversations about the best men’s boots. Their secret? Paying attention to what guys want. The result is not just one but several of the best Chelsea boots for men who want a do-it-all option with staying power.
This model, the Duke, is a SPY favorite. Drawing inspiration from both the dress and work Chelsea boots from the ’60s, the Duke encapsulates the silhouette of those worn by fashionable mod squads with a slightly pointed toe as well as the ruggedness of the old Australian work boot with its studded rubber sole. Coincidentally, it also happens to have a Goodyear welt — named after the son of the man who provided the vulcanized rubber for Queen Victoria’s aforementioned boots.
Many will recognize Thursday from their fierce Instagram ads, but the brand delivers on quality. The Duke, specifically, is available in six colors of durable full-grain leather and waterproof suede and is built on top of an antimicrobial shock-absorbing sole.
Read More: Thursday Boot Company Launches First Cowboy Boot
BEST CHELSEA WORK BOOTS
Blundstone Original #500 Chelsea Boots
Why It Stands Out: In a time when Australia relied on Blundstone as their primary footwear manufacturer, the brand served up this gem — what would later become one of the best Chelsea work boots.
Hot Take: Workwear at its finest, the Blundstone Original 500 Chelsea boots are a mean pair of boots for guys who need to stand up to the outdoors. Distinctly crafted to suit the needs of working people, this chunky-soled brut has found its way onto the feet of denimheads and boot freaks alike.
The legacy of Blundstone Chelsea boots is a testament to the brand keeping up with technology. The Original 500, the stout brown, dons water-resistant leather and a TPU outsole to handle gravel, mud, sod, and more. Despite their appearance, they’re relatively lightweight and easy to move around in. They also have a removable footbed for those in need of even more support from an orthotic insole.
BEST DRESS CHELSEA BOOT
Allen Edmonds Liverpool Chelsea Dress Boots
Why It Stands Out: Allen Edmonds is an American legend for dress shoes. Beyond that, they make one of the best Chelsea boots for jeans to crush that business casual look or a polished look under suit pants.
Hot Take: Quality and comfort are the words here. This Chelsea boot is reminiscent of the many found under those monochromatic suit pants of the 1960s. And though the name tips a cap to The Beatles, this boot is designed the Allen Edmonds all-American way.
Each Allen Edmonds shoe is worked on by 48 different craftsmen who complete 212 steps before the shoe ends up in a box. It boasts a 360-degree bench welt construction and its CustomCork insoles that mold to a foot. The upper is made from European calfskin leather and the soles are vegetable-tanned with rubber tread at the forefoot and heel for traction. Available in dark brown and black, the brand also extends its sizing capabilities to this style which range from a US 6.5 to 15 and widths ranging from B to EEE.
MOST PUNK ROCK
Dr. Marten's 2976 Smooth Leather Chelsea Boots
Why It Stands Out: A later addition to the world of men’s Chelsea boots, the Dr. Marten’s 2976 boots were made famous by the punk scene of the 1970s.
Hot Take: With as much attitude as Sid himself, the Dr. Marten’s 2976 Chelsea boots are still a signature piece to pulling off a Vicious punk outfit today. Their products are so entrenched in punk culture, their slogan even inspired the name of by ’90s punk band, The Bouncing Souls.
Having catapulted to the forefront of must-have styles recently, Dr. Marten’s are best known for their “bouncing,” or air-cushioned soles, making the 2976 one of the most comfortable Chelsea boots for men. Aside from the intense cushion, this boot also features the brand’s classic smooth leather and iconic yellow stitching. As with all Docs, these run in whole sizes only and run large so order the next size down.
BEST SNEAKER SOLE
Amberjack The Chelsea
Why It Stands Out: Amberjack hit the shoe scene in 2022 with three core styles, one of which was The Chelsea. The brand’s differentiator is supreme sneaker soles, and Amberjack makes the best Chelsea boot within that category.
Hot Take: At first glance, most will notice this Chelsea boot has a considerably shorter shaft than others. The height of the shaft actually allows guys to slip the boot on much easier than in traditional styles. After admitting length doesn’t matter, feet are welcomed into a world of comfort.
Amberjack is all about making feet feel good. Inside the boot, they’ve put a heat-activated arch that gets better with more wear. Under that, they’ve added their proprietary TPU sole with great flexibility in the forefoot and an absolute tank of a heel for stability.
This is a Chelsea boot for men who are on their feet a lot and need footwear that works for them. It’s available in nine color options up to a size US 13.
NICEST LEATHER
R.M. Williams Craftsman Leather Chelsea Boots
Why It Stands Out: The R.M. Williams Chelsea boot is another one of the OGs from down under helping the Australian bushmen get work done comfortably for decades.
Hot Take: Another men’s Chelsea boot that stems from Australian workwear, the R.M. Williams Craftsman Leather Chelsea Boot is still made by some of Australia’s best, and it shows. The company’s head of production, Mr. Michael Williams, has been with the company since he was an apprentice 40 years ago and says these boots are his favorite.
The block heels give a little lift and, according to Williams, once “you break in a ‘Craftsman,’ and the leather then starts forming to your foot, I find them so comfortable.” Take it from him and grab a pair. For guys looking for hardcore leather, there’s no better pair.
BEST MATTE FINISH
Thursday Boot Co. Legend Chelsea Boots
Why It Stands Out: Though the Thursday Duke Chelsea boot is fire, the style isn’t offered in black suede. Enter the Legend in matte black. Barney Stinson would undoubtedly dub this legen-wait for it…
Hot Take: Dary. There’s something about a matte finish that reeks of Stinsonesque sophistication and class, albeit, minus the douche factor. The Legend Chelsea boot’s black matte surface on the outside comes from the brand’s Rugged and Resilient leather. Thursday has added a Goodyear Welt for durability and general badassery. These boots also have cork-bed midsoles that form to feet the more they’re worn. They’re handcrafted and built for men who wear their boots out until they’re on their last leg, so there’s no need to treat them gently because Legends never die.
BEST RAIN BOOT
Hunter Boots Original Chelsea Rain Boot
Why It Stands Out: Rain boots are supposed to be fun. The Original Chelsea rain boot is available in up to eight colors to match the miserably wet commuter’s personality, though black seems to reflect the moods of most in a rain storm.
Hot Tak: For guys who love the style and shape of a Chelsea boot but want something to wear in the rain, Hunter’s Original Chelsea boot can withstand all kinds of nasty weather.
A strong rubber sole provides traction and grip, preventing slippage while walking along water-clogged streets. While it’s great to wear as a commuting shoe when there’s a torrential downpour, they work just as well in the sun for those looking to cosplay as Paddington Bear (the yellow can be found at Zappos).
BEST FISHING BOOTS
Xtratuf Steel Toe Legacy Ankle Deck Boot
Why It Stands Out: Men’s Chelsea boots are still technically work boots, but work isn’t limited to the land. Stuff shifts all around the deck with bad chop so having a steel toe reinforcement will put already busy minds to rest.
Hot Take: Initially created for the men and women who work on land and sea in Alaska, Xtratuf boots are meant to be worn no matter how wretched the outdoors are or how crazy the wind, rain, and snow get. And like any brand built for durability and warmth, fishermen in the lower 48 have jumped on these performance-tested fishing boots, even if they aren’t throwing lines too far offshore.
The Xtratuf Legacy Ankle deck boot is a waterproof, slip-resistant Chelsea-style fishing boot made with a non-marking outsole that provides incredible traction even with halibut slime all over the deck. It’s lightweight and can be worn on and off boats. This Chelsea boot is also acid and chemical-resistant. In other words, no matter what hits this boot, it will always look great. Though it’s perfect for fishing, they’re fine to wear on city streets or country roads as well.
BEST VALUE
Bruno Marc Suede Chelsea Ankle Boot
Why It Stands Out: Bruno Marc makes one of Amazon’s best-selling Chelsea boots for men with over 10,000 ratings averaging 4.6 out of 5 stars.
Hot Take: Though boots are a wise investment, there are affordable options for those who are thinking of easing their way into the style. Bruno Marc makes one of the best Chelsea boots for men under $100. Their take on the classic style is tailored strictly toward fashion and pulls out all the right features: elastic goring, a rear pull tab, and a TPR sole.
Available in six color options up to a men’s US 15, their tan is the best Chelsea boot for first-timers. It’ll match with any color chino pants, some stretch denim, or suit pants. If these work, pull the trigger on something fancier as well.
ROI: Price v. Value of the Best Chelsea Boots for Men
Boots are products in which money should be invested. Because of their ties to working men, they’ve been designed to take hits from all angles and, in some cases, outlast the feet that they protect.
The best Chelsea boots of today stay true to their origins, not so much as equestrian wear, but from their adaptation into work boots for the tough terrain of Australia. Many of the styles seen here, from the Blundstone #500 to the R.M. Williams Craftsman and even the Dr. Martens Chelsea boot are priced based on the concept of maintaining their form through any condition. Invest in good boots and they’ll pay off tenfold.
