I can’t imagine a more versatile boot for traveling than the Chelsea boot. First made in the UK during the Victorian era (potentially by Queen Victoria’s very own shoemaker), Chelsea boots were originally worn for both riding and walking before the more modern context of cool kids stomping around the streets of London’s Chelsea neighborhood with these on their feet came to be.
These are the kind of boots that can seamlessly take you from casual days out to more dressed-up evening plans. Because of that, throughout my own travels, I wear Chelsea boots often, from the otherworldly terrain of the Atacama Desert to the meandering, medieval old town of Edinburgh—in fact, I’m wearing a pair there as I type this. And depending on their style (many come with sturdy, durable soles), you can even take some of these on more rugged excursions, too. In the last few seasons, designer labels as well as high-street brands everywhere have been making them in a variety of styles, giving Chelsea boot lovers even more options. But the shoe’s defining design elements—elastic gussets on the side and pull-on tabs at the back—are still intact, and make getting through airport security a breeze. And for travel lovers, that might be the most important feature.
Below, our picks for the best Chelsea boots for men for every type of trip.
Woolrich Chelsea boot
Soft black calfskin leather plus an EVA XL Extralight outsole that’s great on both dry and wet surfaces make this the ideal wear-with-everything boot. You can dress it up or down. You can bring it on any type of trip and not have to hear about being unprepared.
Sizes available: 8-12, including half sizes
Features: Water-resistant, Vibram outsole, removable insole
Amberjack Chelsea boot
Best for all-day sightseeing
Designed in Brooklyn and made in Portugal, these boots are all about innovative, proprietary technology that delivers comfort—the kind that will make hiking around Lisbon’s hills a breeze. High quality leather (super soft buckskin lining), insoles made of heat-activated foam that form around the specific contours of your feet, and a tech-y supportive outsole are just a few of these boots’ best features. Bonus: They come in a variety of easy-to-match colors in both leather and suede.
Sizes available: 7-13, including half sizes
Features: Rubber outsole, removable insole, leather lining
Yves Saint Laurent Wyatt Chelsea boot
Best splurge boot
The rockstar bonafides of these boots, which have a more narrowly sculpted almond-shape toe box, are worth every penny. They’re a classic investment piece with just a little bit of pizazz that sets itself apart, like the one-inch block heel that’ll have you feeling like Bowie and moving like Jagger.
Sizes available: 6-17, including half sizes
Features: Leather outsole, concealed pull tabs, leather lining
Florsheim Lodge Chelsea boot
Best budget boot
Burnished leather plus a rugged suede panel in the back make this an easy everyday choice, whether you’re heading to the office, catching a flight, or strolling around a new city.
Sizes available: 8 to 11.5, including half sizes
Features: Cushioned footbed, rubber outsole, soft Suedetec lining
Boss Lisbon Chelsea boot
Best for destination weddings
Some might argue that laceless shoes, never mind a boot, aren’t right for formal occasions. But this smart, elegant Chelsea says otherwise. A cool choice to wear with a suit for all the weddings you’ll be traveling to, or to pack on business trips.
Sizes available: 7-12, including half sizes
Features: Leather-blend outsole, leather lining
Blundstone 510 Chelsea boot
Best for all terrain
I’ve seen Blundstone’s Chelsea boots everywhere while traveling and on social media, including as the footwear of choice of many vineyard and winery workers, which speak to their durability and stability on both wet surfaces and rugged, uneven farmlands. (There’s a special cushion in there for shock absorption!) Fun bonus: The gussets also come in a variety of colors and patterns, like rainbow.
Sizes available: 3-14, including half sizes
Features: Water-resistant leather upper, durable TPU outsole, removable footbed
Dr. Martens yellow stitch leather Chelsea boot
Best for casual wear
These iconic, slightly rugged boots start off a little stiff but a few wears usually soften the leather to perfection. Other than dressier occasions, they can be worn just about anywhere. I own these boots in cherry, and I’ve worn them hiking. I’m not suggesting you do the same, but in a pinch, they’ll do the trick.
Sizes available: 6-14, excluding half sizes
Features: Air-cushioned soles, Goodyear welted, leather lining
Rothy’s Chelsea boot
Best non-leather option
Made of warm, cozy merino wool and the brand’s proprietary signature thread from recycled plastic bottles, these super comfy boots (with lug outsoles for grip) are eco-friendly and can be tossed in the wash when in need of a deep clean, too.
Sizes available: 7-15, including half sizes
Features: Merino wool upper, removable insoles, grippy lug outsoles
John Fluevog Friday boot
Best lace-up Chelsea boots
If you like the easy, slip-on convenience of a Chelsea but would prefer the look of laces, these are the boots for you. Vancouver’s John Fluevog is known for his creative twists on classic footwear, and this hybrid is no different.
Sizes available: 4-13, excluding half sizes
Features: Water-resistant leather upper, rubber soles from 70 percent recycled materials, can be slipped on or laced up
Brioni shearling-lined Chelsea boot
Best for winter
The casual Vans-like silhouette of these boots are great for daily wear. But thanks to the shearling lining, they’ll withstand the bitterest winter days—pack them as a chic aprés-ski wardrobe staple in Aspen or Gstaad.
Sizes available: 8.5-13, including half sizes
Features: Suede upper, shearling lining, rubber soles
Diemme Balbi boot
Best waterproof boot
Combining the city-slicker vibe of the Chelsea with the outdoorsy legacy of the duck boot (along with its waterproof rubber sole), Italian bootmaker Diemme has created a hybrid shoe ideal for those town-and-country European vacations.
Sizes available: 6-13, excluding half sizes
Features: Suede upper, lugged rubber soles, leather lining
Loewe Chelsea boot
Best statement boot
Perhaps the boots I’m coveting most this season, these electric blue boots are the type of shoes you’ll want to build an entire outfit around. Rarely are Chelsea boots meant to be so head-turning, but how can these help themselves?
Sizes available: 41-45 European, excluding half sizes
Features: Leather upper and lining, triple layer rubber wedge sole
Oliver Cabell Chelsea boot
Best minimalist boot:
The combination of the smooth split-suede upper and the custom-made crepe outsole, which offers increased grip, cushion, and shock absorption, makes these the fuss-free boots of your dreams. The shoe is so sleekly-rendered in all-black that you can wear them with anything, but I especially love them for cool summer evenings with shorts.
Sizes available: 7-13, excluding half sizes
Features: Leather lining, removable leather footbed, rubber outsoles
Mon Dec 12 , 2022
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