20 Best Chelsea Boots For Men: Waterproof, Stylish & Well-Priced

Oliver Cabell is a footwear brand all men worth their stylish salt should be aware of. Not only, like Common Projects, does Oliver Cabell produce a suitably sexy range of sneakers, but it too has some serious men’s chelsea boots to boot. Take this pair, finished in a rather unique truffle colour.

The leather and suede that has gone into their construction has been sourced from Italy, before being hand stitched in Spain. Unusually for a luxury brand, Oliver Cabell breaks down the cost of making each pair of boots, so you can see exactly where your money is going. A well-made pair of boots and ethical production? Sign us up.

Scarosso makes all of its shoes in Montegranaro, Italy and promises to offer customers Italian design and craftsmanship, but without the high price tag commonly associated with such factors. Generally, because of their low margin approach to sales, shoes and boots can only be found in the most popular colours (think blacks and browns) and the same goes for the selection of men’s Chelsea boots.

The Hunter Chelsea boots are modelled on a classic British design and benefit from the Blake Rapid welt for the sole (which introduces a midsole compared to a standard Blake welt, making the Chelsea boots more water resistant). You also get a generously large elasticated side and small nubs on the soles for added traction.

From casual, comfortable walking shoes to waterproof sneakers and everything beyond, Cole Haan is a trusted producer of great boots and footwear. The American brand isn’t afraid to experiment with design, either, as proved by its immensely chunky soles found on select sneakers and boots.

This pair of Gramercy men’s Chelsea boots are far more conventional in their approach, however, being made from premium calf leather, more leather for the lining and a leather sole with added rubber so you don’t go sliding when out on the streets. The company’s own Grandføam can be found in the footbed to provide an extra layer of cushioning, meaning you can wear this leather men’s Chelsea boot all day long.

If you haven’t already heard of Amberjack, then you really should sit up and pay attention. Based in Brooklyn, New York, Amberjack designs some of the most comfortable men’s footwear out there. Using proprietary designs and materials, the company’s Chelsea boots are quite unlike any other you would’ve slipped your feet into.

Aptly named, The Chelsea is a boot that benefits from a sole that combines flexibility and support, to ensure your feet remain comfortable all day long. Heat-activated arch supports provide a memory foam-like feel when you’re walking, and a super soft sheepskin lining only adds to the extreme level of comfort. But, perhaps best of all, is just how little The Chelsea costs, considering what you get. For just under $200, you can own what could be the most comfortable pair of Chelsea boots for men on the market.

Clarks is an absolute boss when it comes to footwear. The British-based brand may be known, in the UK at least, for providing school kids with their back to school essentials, but it should never be overlooked as a provider of quality footwear. With suede and leather options, you can easily score yourself a men’s Chelsea boots for both summer and winter.

The Gobi is an ideal staple, being made from a sumptuous suede nubuck leather for the upper, with a full grain leather liner to cuddle your foot in ultimate comfort. Clarks’ leather and rubber hybrid sole provides just the right amount of bounce and comfort, while also providing great traction.

Some of the most recognisable boots in the business hail from Dr. Martens. The British brand’s iconic sole with yellow stitching is particular favourite of punks and goths, although they’ve also found an affinity with those who simply value comfortable boots that can be worn for hours and hours.

While the lace-up version is undoubtedly the most common you’ll see, it hasn’t stopped ol’ Doc from taking them away to create a Chelsea boot. Benefitting from the same Air Cushion sole that makes them so popular, these men’s Chelsea boots are unmistakably DMs from a distance and rock full grain leather while remaining entirely affordable.

British brand Hunter is known worldwide for its Wellington boots (galoshes or gum boots for international readers) although during its infancy as a company in the 1850s, the company can be considered inventor of the car tyre we know today. The company is now an expert in the use of rubber for footwear, which has allowed it to create more than just humble Wellingtons.

Such as this slim fit Chelsea boot. Constructed from the same rubber that has made Hunter famous, these men’s Chelsea boots adopt a more classic Chelsea boot style, including heel tab. The use of rubber makes them completely waterproof too, making them potentially the perfect pair for city workers in winter.

American bootmaker Rhodes says its boots are designed for those who love to wear a high-top day in, day out, no matter what they’re doing. The company adds they may not compete with whatever fancy and flashy pairs you may also own, but then you would only wear those to high-end occasions. Rhodes handcrafts each pair of boots in either Portugal, Italy or Mexico using calf leather and suede, to result in boots that age gracefully over time.

The Huxley adopts a classic look (and even gets dual pull-tabs) and, being polished as they are, can allow you to wear them with either a suit for formal events or a simple pair of jeans and a t-shirt for weekends on the ranch. A Texon insole with insulation and anti-shock foam gifts all-day comfort, and they’ll even fit like a glove straight out the box. Although, given a week or two of wearing in you’ll forget you have these Chelsea boots on.

British clothing retail giant ASOS is a one-stop shopping destination for practically everything you can think of. With virtually all major brands stocked, including some high-end designer, ASOS makes it easy to do all your shopping online.

The company’s own ASOS Design label stocks many of the classic styles and charges a fraction of the price of more prestigious and recognised brands. These brown leather men’s Chelsea boots with contrasting sole look just as good, however, making use of real leather for the upper. Sure, they might not provide as many years of service as some others, but when you’re paying a quarter of the price (or less in some cases) you can’t really complain.

Mexican bootmaker Unmarked takes its time producing each individual pair of boots, but for good reason. For starters, they’re all handmade at the factory in Leon, Mexico, but on top of that, the vegetable-tanned leather used is put through a slow process from being cut to eventually being moulded into the boots that arrive at your door. They’re a product of love that you can truly feel whenever you put a pair on.

They’re great-looking too, such as the Toro, which use bull hide leather and a storm welt construction. This is an extension of the Goodyear, as it is wider to allow for a more solidified seal to help prevent water from leaking in. Available in a range of colours, these Chelsea boots are ideally suited to being dressed down with jeans or worn underneath a suit.

You can always rely on German fashion label Hugo Boss to inject a little quirkiness into their pieces, providing customers with a chance to stand out from the crowd with unequivocal German style.

This pair of Chelsea boots from Hugo are a prime example. Rocking a conventional suede silhouette, they also receive a neoprene treatment to provide some elasticity so that you can slide them onto your feet.

Founded in California in 2003 but now calling Portland, Oregon home, Keen is a footwear brand that is particularly well suited to the outdoors, thanks in part to the rubber toe bumper found on the majority of its shoes and boots (as well as the Newport Sandal first launched in 1999).

Just on first impressions, the 59 II Chelsea boots look like a tough, rugged outdoor boot and that’s exactly what they are. Premium full-grain nubuck leather protects your feet from dirt and water, while a cushioned midsole makes them comfortable enough for extended walks and hikes. Basically, they’re a pair of men’s Chelsea boots that are more than happy to be treated roughly and thrown around a bit. So have at it.

Italian brand Astorflex has been producing footwear since the 1800s and has often been credited with making “the best desert boots in the world.” Now in its sixth-generation of family ownership, the company strives to be as ecologically-friendly as possible.

The Bitflex is a standout model in the company’s lineup. Taking the traditional Chelsea boot silhouette, Astorflex has given it a memory foam footbed for super soft strides and a ventilated elasticated side panel for sliding them on and off with ease, and for improved breathability. With virtually every colour option you could want being available, you may want to start stocking up.

Not just one to rest on its minimalist white sneaker laurels, Common Projects, being a footwear brand first and foremost has a solid offering of Chelsea boots. This suede pair for example has all the makings of a pair that screams premium.

Not only are they on the perfect side of minimalist – a skill Common Projects is a master of – but they use high-quality materials and colours to make them one of the most versatile pairs of Chelsea boots you’ll ever come across. In true CP fashion, the style, colour and size is stamped on the heel.

British footwear brand Grenson has been fitting the feet of the world for over more than 150 years. It’s no wonder then that it has taken the Chelsea boot and given it its own special twist.

The Declan for example is an exquisitely made pair of leather Chelsea boots, using calf skin leather for their upper and a single piece of leather for their sole. Exhibiting a slightly pointer toe than some other pairs on this list, the Grenson Declan are perfect for those who continue to champion the mod-scene style.

Austrian footwear Zonkey Boot was founded in 2011 with good reason for choosing such an elaborate name. Referencing the donkey/zebra crossbreed, Zonkey Boot aims to combine traditional handcrafting techniques with designs that verge more towards casual and fashionable, as opposed to traditional.

The ZeroThreeThree boots, however, look entirely traditional in their design, but they are oh so lovely. Made from Bavarian Calf leather and hand stained, these Chelsea boots will caress your feet in absolute comfort. A calf leather lining and bovine leather insoles add to their luxuriousness, while also being breathable.

Continuing the domination of the British labels is Paul Smith. The fashion designer is regularly associated with the impeccably dressed gentleman, providing everything from well-fitting sweaters to must-have bags. The same goes for its Chelsea boots, with all manner of styles and materials being used to cater for the style-minded man.

We love these brown suede Canon boots for their just-above-ankle fit and rounded toe. Colour-matching elasticated side panels and soles add their premium look, while the flush-sitting heel tab gives them an overall more streamlined look.

To Boot New York is a footwear brand that hails from America. With footwear-specialist Adam Derrick at the helm, each season’s drop encapsulates what consumers look for is a new pair of shoes, sneakers or boots. Leathers are sourced from France or Italy, where they’re hand-selected and hand-cut to ensure you, the customer, receives only the very best. If you’re after a pair of luxurious brown leather Chelsea boots, To Boot has you covered with the Shelby.

With a low-cut fit that makes them easy-as-pie to take on and off, they’ll happily accessorise any casual or formal outfit. They benefit from a Blake stitch, which sees the outer sole stitched directly to the inner, making them more lightweight than Chelsea boots that use the Goodyear welt.

Tricker’s is Britain’s oldest shoemaker, having been in business for more than 190 years. Every single pair of Tricker’s is made from start to finish at the company’s factory in Northampton, England; a practice which it has carried out ever since its founding.

That therefore means you receive a quality product, such as the Lambourn. Made to resemble a Jodphur boot – a Chelsea boot made to be a riding boot with a rounded toe and heel – they’re equal parts casual and formal. An extra tab on the front of the foot opening helps you slide them on, and once you do, you won’t want to remove your foot from the 100% leather lining.

For yet another luxury option for all your Chelsea boot needs, avert your gaze on to Church’s. This British brand has been in business since 1873, remaining one of the dominant shoemaking forces in the Northampton area. Today the company produces around 5,000 pairs of shoes each week, the majority of which are shipped to international countries.

They may be a tad more expensive than some other pairs of Chelsea boots on this list, but you’re paying for outright quality, such as this pair of Dixton boots. They employ a Superbuck upper and the company’s Last 173 fit. Church’s branding can be found inside and on the sole to let everyone else know how entitled you are.

Synonymous with Australian Outback culture, R.M. Williams is one of the master producers of leather boots. With an esteemed history and age-old production techniques still being used today, when you buy a pair of RMs, you’re investing in something of top-quality, that has been handmade from start to finish.

The Craftsman boot is the iconic RM version of men’s Chelsea boots that adorns the feet of Australians everywhere, as well as international consumers who know quality when they see it.

They’re from a supple Yearling leather, and in true RM style, are made from a single piece, stitched together at the back. A Goodyear welt is used to provide the ultimate in waterproofness and durability, although it also allows them to be resoled should you ever need to.

If you still don’t think there’s a British boot maker for you, maybe Crockett & Jones will be able to charm you. Another centuries-old company, being founded in 1879, the footwear company is a champion of the Goodyear welt, ensuring all its shoes are weatherproof and durable. C&J must be doing something right, as Daniel Craig’s James Bond wore its shoes in Skyfall.

For a classically-styled pair of Chelsea boots, Crockett & Jones has just the thing, with the Goodyear welt remaining a defining feature, this pair of black wax calf leather Chelsea boots will happily protect your feet during winter. A rubber sole ensures you remain planted to the ground and their streamlined look allows them to be dressed up or down.

All of Veldskoen’s shoes are handcrafted in South Africa with locally sourced, premium materials. The brand is committed to crafting shoes that are not only ethically and responsibly made but, feel crazy comfy and provide effortless daily style.

Veldskoen has a small but mighty range of Chelsea boots that are extremely stylish and well-made.