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17 Best Chelsea Boots for Men: Waterproof, Formal, & Cozy Options for Travel

I can’t imagine a more versatile boot for traveling than the Chelsea boot. First made in the UK during the Victorian era (possibly by Queen Victoria’s very own shoemaker), Chelsea boots were then worn for both riding and walking. In the more modern context, these easy-to-slip-on boots experienced a comeback in the 1950s and ’60s when they were worn all over London’s Chelsea neighborhood by the likes of the Rolling Stones.

Given their history as both riding and city-stomping footwear, the Chelsea boots are the kind of shoes that can seamlessly take you from casual days out to more dressed-up evening plans. This versatility makes them a great all-purpose travel shoe. Throughout my own travels, I wear Chelsea boots often: I’ve hiked in them in the Azores (perhaps not the wisest decision) and comfortably rocked them on full days of sightseeing in Mexico City. In fact, they’re the boots I brought to Chile, where I’m writing this right now. 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 edit of the best Chelsea boots for men for every type of trip.

This article has been updated with new information since its original publish date.


Our top picks:


Dr. Martens yellow stitch leather Chelsea boot

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 anywhere. I own these boots in cherry, and I’ve worn them hiking. I’m not suggesting you do the same, but I did survive all those hikes.

Sizes available: 6–14 (excluding half sizes)
Features: Leather upper, air-cushioned rubber outsole, leather and textile lining

Taylor Stitch The Ranch boot

Suede is very trendy right now so if you’re looking for a sturdy alternative to a smooth leather Chelsea boot, we love the rugged look of Taylor Stitch’s Ranch. The whole thing is handmade in Leon, Mexico, one of the world’s premier shoemaking destinations. And it comes with a bunch of quality details that should make these boots last: The Goodyear welt construction means you can re-sole it; the Vibram lug sole helps with traction and stability; and there’s a soft leather lining, plus a cushiony foam insole. And the sumptuous suede will take on a great patina over time. This is a pair you’ll want to wear all the time.

Sizes available: 8–13 (including half sizes)
Features: Suede upper, lug rubber sole, pig-skin lining

Dockers Novato boot

Finding a pair of genuine leather boots under $100 is no easy feat. These sleek Chelsea boots from Dockers are an excellent choice if you’re on a tighter budget. From the outside, it delivers a classic look thanks to the smooth brown leather, the elastic gusset, and the grippy rubber outsole. Style-wise, this is something you could easily wear on all sorts of trips, whether you’re heading to a business meeting or on a long-weekend city break. Inside, it features a quilted footbed and a moisture-wicking sock cover for added comfort. Overall, you get a lot from this budget pick.

Sizes available: 7–13 (including half sizes)
Features: Leather upper, moisture-wicking synthetic lining, rubber outsole

Suitsupply black boot

The glamorous bonafides of these boots, which have a more narrowly sculpted toe box plus a slight chunky heel, make them a great option to wear with a more formal outfit, like a suit for a destination wedding.

Sizes available: 7–13 (excluding half sizes)
Features: Leather upper, leather sole, leather lining

Blundstone All-Terrain Thermal Chelsea boot

I’ve seen Blundstone’s Chelsea boots everywhere lately, including as the footwear of choice of many vineyard and winery workers, which speak to their durability on both wet surfaces and rugged, uneven farmlands. I’ve also seen them at ski resorts and on city streets—making them a great pair of boots for all sorts of global adventures. The ones featured here are waterproof and come with a Vibram sole for an extra bit of grip.

Sizes available: 3–14 (including half sizes)
Features: Waterproof leather upper, Thinsulate and leather lining, Vibram outsole

Greats The Bowery Chelsea

If you want a classic-looking pair of boots with a trendy edge, we love the oversized aesthetic of the Bowery from Brooklyn-based shoe brand Greats. The smooth leather exterior is incredibly sleek so you know it’ll be easy to pair it with a variety of outfits, but we love the eye-catching luge sole: It offers a stable grip, but the exaggerated silhouette makes it a bit more fashion-forward.

Sizes available: 7–12 (excluding half sizes)
Features: Leather upper, leather lined, lug rubber outsole

Banana Republic Burnished Italian Leather Chelsea boot

This ruggedly handsome Chelsea is a great choice if you’re looking for a chic boot you’ll wear daily. The burnished Italian leather upper has a beautiful worn-in look that will complement everything from jeans to chinos to more formal trousers. The blake-stitch sole means these aren’t going to be too heavy, which is fantastic for travel.

Sizes available: 7–13 (including half sizes)
Features: Leather upper, lug rubber sole, leather lining, cushioned footbed

Ariat Booker Ultra Western boot

Wanna add an unexpected (and stylish) western flair to your Chelsea boot? Go for these blue suede shoes from California’s Ariat. The shoe has that stretchy side gusset that’s classic Chelsea, but the intricate stitch work on the vamp, the slightly chunky block heel, and the square-ish toe box give each pair a hint of cowboy personality. Wear it under a great pair of denim and a flannel shirt if you really wanna play up the western fantasy.

Sizes available: 7–13 (including half and wide sizes)
Features: Leather upper, Bantamweight sole, synthetic lining, cushioned footbed

Oliver Cabell Chelsea 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

John Varvatos Freeman Chelsea boot

If you’re splurging on a designer boot, we love the Freeman from John Varvatos, because while it still looks like a traditional Chelsea, they’ve added rockstar elements that make it a bit more unique: The slouchy suede treatment is eye-catching without being over-the-top, and the rubber outsoles offer a ton of grip. This comes in two classic colors, but we’re really into the minimalist vibe of the all-black pair.

Sizes available: 8–12 (including half sizes)
Features: Suede upper, leather lined, rubber outsole

Sorel Carson Waterproof Chelsea boot

A budget-friendly boot from Sorel that’s made to be put through its paces, the suede here is waterproof and the seam-sealed construction is meant to keep moisture out. Plus, the malleable rubber sole will keep you sturdy if you’re ever called to jump over wintry puddles or if a mild hike through the tropics is in your future. Color options for these boots include classic shades of brown, but we’re partial to the refreshing grayish green that Sorel calls “major/ancient fossil.” These boots look very safari-ready, too.

Sizes available: 7–15 (including half sizes)
Features: Suede and textile upper, textile lining, rubber sole

Ugg Burleigh Chelsea boot

If you’re in the market for a winter-ready boot, Ugg’s Burleigh is lined with a cushy wool-blend textile that will keep your feet extra toasty. These boots have all the Ugg details like the fuller toe box and the waterproof suede. We love the addition of the Spider Rubber Pods on the thicker Sugarcane EVA outsole—they help with traction as you walk over slippery surfaces. We also love these post-ski when your feet could use a comfy break from being strapped into heavy boots.

Sizes available: 7–15 (including half sizes)
Features: Waterproof suede upper, UGGplush sockliner, Sugarcane EVA midsole

Woolrich New City 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 all-weather boot. (The chunkier sole is super trendy, too.) You can dress the pair up or down, and bring them on any type of trip without worrying about being unprepared.

Sizes available: 6–13 (including half sizes)
Features: Leather upper, removable insoles, two-tone XL Extralight EVA sole

Morjas The Chelsea boot

Most Chelsea boots are better suited for casual outings, but this super sleek one from Morjas is perfect for formal occasions. The supple, smooth calf leather looks immediately fancy, and the leather lining adds a luxe feel when on, too. While this does have a more dressed-up vibe, we like the inclusion of a sturdy rubber sole—most boots that go for elegance usually come with leather outsoles, which are super chic but are not always as grippy as rubber.

Sizes available: 5.5–13.5 (including half sizes)
Features: Leather upper, leather lined, rubber outsole

Florsheim Lodge Chelsea boot

Burnished leather plus the 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, exploring a new city. 
Sizes available: 7–14 (including half sizes)
Features: Leather upper, rubber sole, Suedetec lining

Amberjack Chelsea boot

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

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