Best Hybrid Chelsea Boots for Men: LUCA Terra Slip On Chelsea Sneaker Boot

These are not shoes for any man, no these shoes are for men who want something no one else has. If you’re daring enough Aurélien has made your dream shoe. Part sneaker, part chelsea boot, (and all comfort) these are ready for all day outings and stylish dinners. 

Now, while the look of these shoes is certainly unique, it’s best to remember they run on the casual side – we wouldn’t recommend wearing these with a suit. If you’re looking for something truely universal, we would suggest something else on this list.

However if you’re ready to jump in, these chelsea boots for men would do wonders paired with a pair of slightly tapered pants or straight leg jeans. All leading the eye down to the prize possesion (…the shoes that is).

Best Winter Chelsea Boots For Men: Blundstone 550

Ah, the classic has arrived. Blundstone’s have been on the market for years (since 1870 if we’re counting) but have recently blown-up as the perfect utliarian shoe. Going for a hike? Blundstone’s. Going out for some drinks? Blundstone’s. A first date? You guessed it, the Tasmanian king, Blundstones.

These boots will not follow you to work but they will follow you everywhere else. The soft leather will mold to your foot and the structured rubber sole will keep you secure to the ground (even after a few drinks). In our experience the shoes are realatively easy to clean and maintain, Blundstone even has a polish if you’re looking for them to shine and to protect the leather for longer (especially in the winter).

Best Classic Chelsea Boot: Grenson Declan Boots

Grenson has established itself as one of the best made in Britain shoe brands, championing quality and classic design over trends.

True to form, its men’s Chelsea boots are a masterclass in fuss-free craftsmanship, with each pair taking eight weeks and 200 individual operations to complete.

Best Budget Chelsea Boots For Men: H&M Chelsea Boots

Fast fashion stalwart H&M may be best known for its wallet-friendly wares, but the Swedish firm’s premium line provides the perfect happy medium for those looking to go high-end on their best boots without forking out half a month’s salary.

Check out its line of men’s Chelsea boots for swanky stompers at a fraction of the cost that equivalent designer styles would cost you.

Best Casual Chelsea Boots for Men: Dr. Martens 2976 Smooth Leather Chelsea Boots

Ask anyone on the street, and they’ll tell you that Dr Martens produces some of the the best shoes in the world, but its comprehensive catalog of rebellious styles spans further than that its iconic 8 eyelet lace-up.

The brand’s men’s Chelsea boots take the essence of the original and add some trademark edge to de-gentrify the style.

Best Waterproof Chelsea Boots For Men: Hunter Original Chelsea Boots

The quintessential Wellington boot brand, Hunter has smartly adapted the festival essential in recent years for the men’s Chelsea boot crowd.

Made just like its wellies, using a strong vulcanized rubber to keep your feet safe from the elements, the boots are cut at the ankle for a more stylish way to take on the typically muddy British countryside.

Best Luxury Chelsea Boots For Men: Saint Laurent Wyatt 30

In the quest for the ultimate designer Chelsea boot, the book well and truly stops with Saint Laurent.

The luxury brand has made its name on the back of the Hedi Slimane era rock ‘n’ roll aesthetic, and as such, produces some of the best men’s Chelsea boots on the market. Pair with a leather jacket and an IDGAF attitude.

Best Pointed Toe Chelsea Boot For Men: Beckett Simonon Bolton Chelsea Boots

An all-weather shoe that doesn’t look like the clunky boots your mom bought you in middle school? We didn’t think it was possible either but Beckett Simonon has crafted your best basic. The leather soles with steel shank and wider (more comfortable) pointed toe box is what really sold us.

This shoe is incredibly rated amoung buyers as well, which is an added bonus. The best chelsea boots for men are also easily incorporated into your wardrobe. Our favorite would be with some Japanese denim and black denim jacket to create a simple yet stylish contrast. Pair it with your best t-shirts but for the love of god don’t forget to roll your pant legs.

Best Suede Chelsea Boots For Men: R.M. Williams Craftsman Chelsea Boot

Australian brand R.M. Williams has a history that stretches back to 1932, so flash-in-the-pan footwear this is not. From its assortment of Chelsea boots for men, expect a typically laid-back Aussie design with impeccable performance underfoot thanks to Goodyear-welted soles.

Best Of The Rest

Timberland Redwood Falls Chelsea Boot

American outdoor brand Timberland is an industry-leading eco-conscious footwear company. And it’s this dedication to the cause that led to the creation of its men’s Chelsea boots, which are made out of leather from a Leather Working Group Silver-rated sustainable tannery.

As well-crafted as its iconic worker boots, the brand’s tree logo imprint above the heel makes for a neat feature on a traditional shape.

UGG Biltmore Chelsea Boot

Fans of well-made and comfortable footwear (so that’s everyone, then) will no doubt be familiar with UGG. The footwear retailer’s frankly utilitarian take on Chelsea boots for men is refreshing to see against the typical shiny leather style.

Clarks Clarkdale Easy Chelsea Boot

If you’re anything like us, your first meeting with Clarks will have been in the run-up to your first year at school. Luckily though, there’s plenty of footwear on offer that’s adult-friendly too.

The brand’s men’s Chelsea boots, like its Chukka boots, deliver the same solid, no-fuss appeal, but with advanced sole technology that also promises unmatched comfort.

ASOS Cuban Heel Western Chelsea Boots

ASOS is pretty much the Aladdin’s Cave of menswear, so whether you’re feeling skint or flush, adventurous or pared-back, it is sure to have a pair of men’s Chelsea boots that will appeal. It’s practically impossible to leave empty-handed (or footed).

Aldo Collen Chelsea Boot

If you’re looking for top-notch smart-casual shoes without having to step off the high street, you can’t go far wrong with Aldo. At an affordable price point for a well-made shoe, the Canadian brand’s range of simple but stylish men’s Chelsea boots are a failsafe option that will slot in with any wintry looks you’re cooking up.

River Island Chelsea Boots

River Island has long been in the game for over 60 years, but there’s nothing outdated about its expertly crafted boots, which take that time-tested knowledge and combine it with subtle design tweaks for the perfect fusion of tradition and trend.

Church’s Goodward R Chelsea Boots

With a history stretching back well over a century, it’s no exaggeration to say that you’re always in a safe pair of shoes from Church’s.

For fans of heritage, craftsmanship and obsessive attention to detail, you’ll struggle to find a finer pair of men’s Chelsea boots.

Frye Dylan Chelsea Boots

What do Chris Hemsworth, Chris Evans, and Miles Teller all have in common? Well, apart from being Hollywood deities, they’re also all fans of heritage American bootmaker Frye.

Having previously made shoes for soldiers in the Civil War, expect men’s Chelsea boots made out of rough suede and with sturdy moccasin constructions that go against their posh, polished Anglo cousins.

Boss Colby Chelsea Boots

Hugo Boss bootmakers can boast of putting footwear on royal feet the world over. If you’re looking for the perfect men’s Chelsea boots to pair with any outfit, you’d be hard pushed to find a brand with more thumbs-ups from the most discerning of men.

Red Wing Weekender Chelsea Boot

Handmade in the USA, Red Wing’s work boots offering puts good ole American manufacturing front and center, meaning each pair of men’s Chelsea boots from this stateside shoe supplier have rugged functionality at their core. The fact that they look the part is a welcome bonus.

Oliver Cabell Chelsea Boot

If you thought minimalist sneakers were where the Oliver Cabell canon ended, let us introduce the English label’s equally lust-worthy men’s Chelsea boots. While we certainly love the OC Low 1s, the brand has earned a place in our hearts.

Available in both leather and suede, they’re made with the same contemporary stealth wealth design ethos, while still staying true to their minimalist roots.

A Brief History of Chelsea Boots for Men

Harking back to the 1850s, ankle boots (as they were simply known then) were invented by Queen Victoria’s shoemaker, J. Sparkes-Hall, as an alternative to lace-up riding boots, which were almost impossible to remove unaided. The Victorians were suckers for practicality as well as prudishness so they added a handy elasticated ankle to the riding boot shape.

The name we use today to describe these stylish stompers unsurprisingly hails from London’s well-heeled Chelsea area, where they were the de facto king of footwear during the 1950s and 1960s on King’s Road, be it on the Sloane Rangers that lived there, or the Mod subculture riding through.

It’s little wonder that they went mainstream either, considering they’re one of the most versatile types of shoe a man can own; the sleek silhouette looking just as good polished to a shine as left gently scuffed for a rock ‘n’ roll patina.

How To Wear The Best Chelsea Boots For Men

As with any menswear item considered a heritage piece, you’ll need to tread carefully when styling to avoid going into turbo toff mode. Gooding’s advice for going more rockstar than rah? “Wear men’s Chelsea boots casually with jeans, a white T-shirt and a ‘thrown-on’ shirt.” Simple.

If you’re looking to sharpen up your act, however, both what you wear and the boot’s ankle height come into play. “A taller ankle height is very on-trend and adds a smarter feel for a sharper look,” adds Gooding. “These look great when worn with slim jeans, a crisp Oxford shirt and a smart wool coat.”

As for where you’ll find the best, try some of the men’s boot brands included in this list, which deliver on style, substance, and a little more style.