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Chelsea boots are arguably the most versatile boots on the planet. They’re classy enough to wear with slacks and a sport coat, casual enough to rock with jeans and a T-shirt, and oh-so-comfy for everything in between.
The secret to these adaptable boots lies in the elastic gore that you’ll find on the sides. The twin gores make it easy to slide in and out of the boot, and provide a snug fit that eliminates the need for laces.
Whether you’re looking for a pair of boots for work, weekends, or all of the above, we’ve got you covered. Here’s a list of our favorite Chelsea boots for men, with options for every taste and budget.
What to Look For
Elastic gore: That’s what makes it a Chelsea boot. The gores should make the boot easy to slip on and provide a snug fit
Premium leather: Quality leather ages like a good whiskey and develops a rustic patina over time
Fit: You’ll probably need to size down for a snug fit, and it’ll take a few outings to break them in before you hit the sweet spot for comfort
Resoleable: Premium boots with a welted construction are resoleable, which significantly extends the life of the boot
The Best Chelsea Boots Under $150
Steve Madden Proven Chelsea Boots
What we dig: The best damn value for a classy Chelsea boot, period
Finding a solid pair of Chelsea boots under $200 is hard enough, so we lost our minds when we found these Steve Madden Proven Chelsea Boots for less than $100. They’re classy, comfortable, and easy to slip on thanks to the elastic gore.
The black leather looks dapper as hell, but it’s the camel leather that’s calling our name. Either way, this is a versatile set of Chelsea boots that you can easily dress up or down to suit the occassion.
Timberland Logan Bay Chelsea Boots
What we dig: A comfy-casual boot with grippy rubber outsoles for maximum traction on wet, uneven terrain
These sleek Chelsea boots feature a premium, water-resistant leather upper and Gripstick rubber outsole for sticky traction on all surfaces. They’re easy to slip on when you’re rushing out the door, and the anti-fatigue footbed ensures all-day comfort.
The Best Chelsea Boots Under $200
Astorflex Bitflex Boots
What we dig: Handmade Italian boots with premium European leather and eco-friendly construction
You can never go wrong with a pair of boots from Astorflex. These guys have been handcrafting premium footwear in Northern Italy for six generations, so they know a thing or two about making a fine pair of boots.
The Bitflex Boots are crafted with premium European leather that’s aged for 30 days in an all-natural medley of powdered mimosa, oak bark, and water. The leather is softened with natural ingredients to create a smooth, supple leather upper, then they wrap it up with a leather sole and stacked heel for a sophisticated finish.
The Bitflex Boots are available in eight colors, so it’s easy to find the perfect pair to round out your wardrobe.
SeaVees Coronado Boots
What we dig: The kings of slip-on shoes deliver a hybrid boot/shoe that’s unbelievably comfortable and oozing with California cool
SeaVees are renowned for their comfortable slip-on shoes, so it shouldn’t be too surprising that the California company offers a great slip-on boot.
The Coronado Boot blends the style of Chelsea boots with the comfort of slip-on shoes, creating a hybrid footwear that’s far more cozy than your average pair of boots.
Up top, the Coronado Boots feature leather uppers with twin elastic gores and a rear pull tab for slip-on convenience. Inside, the memory foam footbed is lined with soft cotton and perforated with cooling airflow channels for maximum comfort.
On the bottom, the Coronado Boots employ a gum rubber outsole for a softer ride, longer wear, and optimal flexibility. The signature herringbone outsole also delivers top-notch slip resistance, making these boots an excellent choice for uneven terrain.
Thursday Boot Co. Duke Boots
What we dig: A versatile pair of Chelsea boots from a classic American boot maker
Looking for a classic pair of Chelsea boots with a dash of American craftsmanship? Check out the Dukes from Thursday Boot Co.
The Dukes are handcrafted in the USA, boasting a resoleable Goodyear welt construction and full glove leather interior lining.
These versatile boots deliver all-day comfort thanks to Poron antimicrobial shock-absorbing insoles and cork bed midsoles, while the durable studded rubber outsoles offer excellent traction.
Wolverine BLVD Chelsea Boots
What we dig: A ruggedly handsome pair of Chelsea boots that are just plain bad to the bone
When it comes to long-lasting boots, it’s tough to beat the longevity of Wolverine boots. These guys are known for their thousand-mile boots, and all of their boots are built to last for decades.
The Wolverine BLVD Chelsea is a staple for boot-lovers. It’s classy enough to wear in the board room, casual enough to dress down with a pair of jeans, and comfortable enough to wear all weekend.
The BLVD Chelsea boots feature rich, full-grain leathers with sheepskin lining — both of which only get better with age. The Goodyear welt construction means they can be resoled for decades of wear, and the rubber lug outsole delivers more than enough grit to keep you centered on slippery, uneven terrain.
The Best Chelsea Boots Under $300
Rhodes Footwear Huxley Boots
What we dig: Soft, supple calf leather that ages like a top-shelf bottle of scotch
The Huxley Boots from Rhodes Footwear look fantastic and feel even better. The premium calf leather uppers are ultra-durable, odor-resistant and breathable, while the Texon insole with thermal insulation and anti-shock foam keeps you cozy from sunrise to sunset.
There’s no breaking-in period with the Huxley Boots, so you’ll enjoy unrivaled comfort straight out of the box. They’re handcrafted in Portugal, and the resoleable Blake stitching construction offers a flexible sole for a smooth ride.
The Jude Chelsea Boot By Taft
What we dig: A refined pair of Chelsea boots that make a striking statement when you walk into the room
The Jude Chelsea Boots are handcrafted in Spain, featuring luxurious Spanish suede that’s tanned and milled in Almansa.
Slip your foot inside and you’ll discover a leather-lined interior with a cushioned airbed for comfort. On the bottom, the sole is double-stacked, full-grain leather with rubber inserts for optimal grip and durability.
Nisolo Chelsea Boot
What we dig: These beauties are handcrafted in an ethical, family-owned factory with premium leather
The Nisolo Chelsea Boots are handcrafted in Leon, Mexico with Goodyear welt construction and inset rubber grip. Your feet will be wrapped in luxury leather from top to bottom thanks to a leather upper, leather lining, and soft leather insole.
Expect a snug fit the first time you slip on these Chelsea Boots. It’ll take 3-5 wears to break them in before you reach the point of optimal comfort.
The Best Premium Chelsea Boots
Allen Edmonds Liverpool Chelsea Boot
What we dig: An iconic British boot with a healthy dose of American attitude and authentic 60’s style
If you’re looking for dress boots, check out the Liverpool Chelsea Boots from Allen Edmonds. Sure, you can wear these with a pair of jeans, but these premium leather boots look their best with slacks and suits.
The Liverpool Chelsea Boots feature a 360° Bench Welt construction with CustomCork insoles that mold to your feet for a custom fit. They’re handcrafted in Port Washington, Wisconsin with soft calfskin leather and a V-tread tap sole for flexibility and discrete traction.
R.M. Williams Comfort Craftsman Boots
What we dig: Handcrafted, authentic Australian Chelsea boots with durable yearling leather
R.M. Williams has been crafting fine footwear in Australia since 1932. The family-owned business’s dedication to quality is unrivaled, to the point that every boot passes through 80 pairs of hands during the construction process.
The Comfort Craftsman Boot incorporates supple suede leather with a recraftable welted non-slip sole. The entire boot is crafted with a single piece of leather, and you’ll enjoy a comfortable fit with the leather insole and padded heel lining.
More Tips On The Best Boots For Men
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