The Most Stylish Chelsea Boots For Men

Chelsea boots represent a brilliant combination of rugged and smart-casual styles, and that’s why so many men love them. They bring everything to the table at once; hard-wearing soles, slick silhouettes, comfortable insoles, and an all-terrain grip. A jack-of-all-trades, a good pair of Chelsea boots goes just as well with a suit and tie on an evening out as it does with gritty hiking gear and a muddy country trail. If you’re looking for your first ever pair or just the perfect addition to your current collection, then this list is a great place to start.

OUR RECOMMENDATIONS

BEST MEN’S CHELSEA BOOTS FOR WIDE FEET

Not all bootmakers cater to wide sizes, but the Thursday Boot Company has stepped up with aplomb with their flagship Duke Boots, available in wide EE or EEE sizes. These lovely Chelsea boots have extra-long side gussets, too, giving them the ability to contour to a foot of any shape or size. Available in 6 striking styles, from honeyed suede to chocolate brown, there’s a great boot here to fit any man.

BEST MEN’S CHELSEA BOOTS FOR WINTER

A powerful pair of boots for stomping through snow or taking on icy pathways, the Blundstone Super 550s are super-sturdy and built to last. They’re a rugged, rustic pair of boots with great traction on their grippy all-terrain outsoles, and on top of this, they also have a comfortable cushioned footbed and double-tug pulls to help you keep them on nice and tight. What’s more, they’re also leather lined, meaning they’ll keep your feet nice and warm in the coldest of weather conditions. 

BEST MEN’S CHELSEA BOOTS FOR WALKING

If you’re taking on long walks or country strolls, then you’ll need a pair of boots both comfortable and hard-wearing. The Timberland Stormbuck Chelsea Boots bring an ideal combination of both of these factors to the table, with a gusseted leather upper that’ll stretch nicely over a few wears and a slim sole with strong traction that makes for an easy step. Available in burnished brown or smooth black leather, they’re a great-looking pair of boots too.

BEST MEN’S CHELSEA BOOTS FOR RAIN

For wet weather use, the R.M. Williams Gardener boots are a classic pick, and for a good reason. They’re the perfect blend of hard-wearing materials and homespun style, with a thick outdoorsman’s sole capable of taking on wet weather and a sleek leather upper that’ll keep off the rain, no trouble. The soles are provided and welted by Goodyear, so they’re the absolute best in the business in terms of overall fidelity. 

BEST AFFORDABLE CHELSEA BOOTS FOR MEN

The best Chelsea boots are not always the most expensive, and Clarks’ Men’s Paulson Up boot proves that you can get a premium quality product for a budget price. This lovely boot is crafted from hard-wearing leather with a synthetic rubber heel and has a durable TPR outsole along with interior heel support. The stitching shown here is just as well done as what you see on much more expensive boots, and the Ortholite footbed technology makes them just as comfortable to wear as any other option on this list.

THE LUXURY PICK

If you’re looking for the most luxurious Chelsea boots you can find, you won’t do much better than the R. M. Williams Chinchilla boot. Handcrafted in Australia from European crust leather, these sumptuous square-toed boots have a gorgeous burnished finish and a striking two-tone leather heel. A full kidskin lining makes them a dream to wear, and the colors of the boot are beautifully accentuated thanks to the hand-applied Italian dye used in the finish.

1. Dr. Martens Graeme II

Doc Martens are a recognizable classic all across the globe, but they offer much more than just their stock boot. Their Graeme II is a Chelsea boot that takes the classic Doc Martens look and streamlines it for a slip-on closure, with a single branded pull-tab and elasticized side panels. These boots aren’t just good to look at; Doc Martens also guarantee their boots for a lifetime, meaning you can take them into a store for repairs should they suffer any wear and tear.

2. Common Projects Suede Chelsea Boots

These sandy suede Chelsea boots from Common Projects come in a lovely pale brown colorway, with a gold-stamped serial number in the interior heel. The single pull-tab can be easily tucked into the back of the boot when on the go, and the brown leather lining of the upper ankle provides a nice contrast to the overall look.

3. R. M. Williams Yard Boot

Available in Dusty Ochre or Brushed Grey colorways, the R. M. Williams Yard Boot uses a round-toe design for a cool, comfortable shoe. With a rounded knit gusset that curves around the ankle, these are a supremely comfortable pair of men’s designer Chelsea boots. The embroidered tug is a lovely finishing touch.

4. Jack Erwin Ellis Boot

These black Chelsea boots from Jack Erwin are hard-wearing and good-looking, with an all-leather upper and a durable rubber sole sure to see you through many days of strolls in the city and walks out in the country. With a single-tug design, these are simple and restrained, and they’re also available in brown full-grain leather and brown leather suede, just in case you fancy something a little different.

5. Astorflex Bitflex Chelsea Boot

With a traditional design, these brown Chelsea boots from Astorflex might seem like any other pair, but what makes them really special is their eco-friendly construction. Handmade in Italy, these high-fidelity boots use Beeswax-treated nubuck leather, along with sustainably sourced rubber soles, for a green shoe that keeps your feet comfy without harming the environment.

6. Saint Laurent Black Wyatt Chelsea Boots

If you’re looking for platform Chelsea boots that give a little bit of extra height, then the Saint Laurent Black Wyatt boots are the perfect pick for you. With a tall 1.5” heel, they’re sure to give you a lift, and a hidden tug gives them a sleek overall silhouette. Elasticized gussets make them a comfortable fit for any foot, and the lovely calfskin leather will become soft and fitted throughout a few wears.

7. Scarosso Chelsea Boots

These boots represent another pair of traditional suede Chelsea boots. Scarosso’s offering sports a low-heel look for something a bit more subtle. With a brown mocha colorway and an Almond toe design, these boots are made more for blending in than standing out and pair perfectly with any number of outfits, whether you’re dressing up or dressing down.

8. R. M. Williams Comfort Turnout Boot

Another excellent pair of Chelsea boots for men from R. M. Williams, the Turnouts are available in 2 colorways, black or bark brown. They have a rounded toe for a restrained top-down profile and a padded insole for your comfort. With a fully welted sole, they’re sure to take a beating without much trouble, and the hard-wearing leather should last you nicely through the years.

9. Oliver Cabell Lion Chelsea Boot

The Lion Chelsea boots from Oliver Cabell are a pair of men’s designer Chelsea boots with a hand-stitched sandy suede upper, evoking Saharan tones in an otherwise Western shoe. The woven elasticized gussets provide another rustic touch, while the crepe rubber soles finish the boot with a slick and sturdy edge.

10. Blundstone Super 550 Chelsea Boots

A sturdy pair of Chelsea rain boots that can stomp through a fair few puddles without trouble, the Blundstone Super 550s are pleasantly chunky and have plenty of rustic charm. With a grippy all-terrain outsole and a cushioned footbed, they’re not just road-worthy but also supremely comfortable. Meanwhile, the lovely exterior leather has a delightful distressed look, giving this pair of boots a healthy dollop of homespun charm.

11. Nisolo Javier Chelsea Boot

With a slick European look and a high sheen brandy colorway, the Nisolo Javier Chelsea boots are stylish to a tee. They have a sleek, sloped profile, which arches delicately down to their two-tone sole – a nice touch to give some variation to the overall color palette. These boots are also available in brown and black, and all three colorways have a high-sheen all-leather upper.

12. Bruno Marc Suede Chelsea Boot

With a wide bevy of styles available, including their stock black Chelsea boots, Bruno Marc’s excellent collection truly has something for everyone. Several styles include flashy two-tone soles and colored stitching, and all of them come equipped with an EVA foam footbed for a soft step with every stride you take. A low-profile tug keeps the ankle-line restrained, while the synthetic sole is perfect for all weather conditions.

13. Dr. Martens Hardie Boot

Another fine pair of clogs from Doc Marten in a men’s Chelsea boots style, the Hardie Boots are thick-soled stompers with a double-tug pull and a low-profile ankle cut. These boots have sturdy, air-cushioned soles, meaning they’re much more comfortable than they look, and thanks to the added side-stitch construction, they’re some of the most well-crafted Chelsea boots out there.

14. R. M. Williams Gardener Chelsea Boot

These brown Chelsea boots from R.M. Williams are perfect for use as a casual or outdoorsman’s boot, with a thick and durable sole and a classic gardener’s boot profile. They use a double-tug pull this time around to help you get a perfect fit, and the soles are provided and welted by Goodyear, making them some of the best Chelsea boots for men in terms of long-lasting durability.

15. Clarks Paulson Up Chelsea Boot

Clarks’ shoes are always smart in looks and price, and their Up Chelsea boots are another great low-budget piece of footwear. Available in 6 colorways, including suede and leather options, these Chelsea boots for men come equipped with super-soft Ortholite footbed technology for an ultra-comfortable instep. They also have heel support to keep your joints and ankles free from strain, making them a great choice for health-conscious wearers.

16. Beckett Simonon Bolton Chelsea Boots

Available in four colorways, from black to Bordeaux red, these single-tug Chelsea boots for men from Beckett Simonon have a stripped-back design with a high-ankle cut and a smart overall aesthetic. The best thing about these boots is their longevity; all of Beckett Simonon’s shoes are completely resoleable, meaning you can give these boots a new lease of life even decades down the line. You’ll never need to splash out on a new pair when you can simply make do and mend!

17. Thursday Boots – Duke

The Duke from Thursday Boots are a great pair of shock-absorbing Chelsea boots, available in a variety of honeyed suede shades or with smooth leather uppers. Here, the soles have been layered with cork-bed midsoles to aid in shock absorption, and comfort insoles are also included. Available in variable widths, there’s a pair here to suit any foot.

18. Blundstone Round Toe Chelsea Boot for Men

Another great pair of Chelsea rain boots from Blundstone, this Round Toe option is a nice spin on their other designs, with a double-tug design meant for easy slip-on and slip-off removal and an ankle-length cut designed to keep your cuffs dry. The upper leather construction will wear nicely with time, while the synthetic sole is the perfect defense against wet weather.

19. Blundstone BL550 Boot

Blundstone has smarter options, and the BL550 Boot is a nice variant on their normal rain boots. A pair of brown leather Chelsea boots in a lovely walnut colorway, the BL550s have a classic overall silhouette that blends sturdy stitched leather with a smart almond toe for a nice balance of function and form. Double-tugs make them easy to pull on, and the gusseted side panels give a nice amount of stretch.

20. Timberland Men’s Stormbuck Chelsea Boots

Timberland makes a great range of boots these days beyond their classics, and their men’s designer Chelsea boots are another great addition to their already strong collection. Available in burnished brown or smooth black styles, these leather Chelsea boots are an eco-friendly option made from sustainably sourced materials and recycled rubber.

21. Grant Stone Chelsea Boot

Grant Stone’s staple black leather Chelsea boots bring together a few nice features that we’ve seen so far on this list, including Goodyear welted soles for premium durability and cork filler for a shock-absorbing step. The fit runs large here, so they’re perfect for men who wear half-sizes and struggle to find a good fit, or just for those who want a little bit of extra room.

22. R. M. Williams Craftsman Boot

Available in dark tan, chestnut, or smooth black styles, the R. M. Williams Craftsman boots are a fine pair of men’s Chelsea boots stitched from yearling leather, with a thick all-leather sole. These boots have a unique silhouette thanks to their chisel-square toe, and they’re super sturdy too, all thanks to their hand-sewn welt, making them a great all-purpose pair of footwear.

23. R. M. Williams Chinchilla Boot

Last but not least come another great pair of boots from R. M. Williams. The Chinchillas sport a chisel-square toe just like the Craftsmans, but they differ in a couple of key ways, including a double-tug pull for an extra-close fit. The Chinchillas also have a lovely burnished finish, which pairs beautifully with the two-tone leather sole and emphasizes the curved profile of the boot. These are a truly luxurious choice for those who want the best boots money can buy.

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