You can trace the roots of my Chelsea boots obsession back to my mid-twenties when Primal Scream’s Bobby Gillespie and a nondescript shoe shop changed my life.
I needed new boots but all the lace-up ones in-store were hideous. All apart from a rock’n’roll pair of black suede Chelsea boots that looked vaguely like the ones I’d seen Bobby wearing in a magazine, looking cool. So, I took the plunge and leapt off the lace-bound diving board. I soon discovered that Chelsea boots come in every conceivable style: dressy, dandy, casual, cowpoke - you name it. The Chelsea is the ultimate no-nonsense boot; the last word in impeccable brilliance.
The first elastic-sided boot is considered to have been designed by Queen Victoria’s bootmaker, J Sparkes-Hall, who created them so her Majesty could pull them on and off easily. However, it didn’t acquire the name “Chelsea boot” until the Swinging Sixties when the beatniks along the King’s Road all seemed to be sporting this groovy, elastic-sided footwear.
But how can you tell if what you’re about to buy is any good? As a general rule, you get what you pay for. For footwear that will last, be prepared to fork out. Top quality boots are made by skilled craftspeople who don’t cut corners.
While the Italians turn out incredible footwear, luckily for Brits, many consider us the best shoemakers on the planet. Set your compass firmly for Northampton, where revered heritage brands such as Church’s, Grenson and Tricker’s have been crafting brilliant boots for centuries.
You might also need a quick 101 on a couple of perplexing technical details. Should you get leather soles? In short, not necessarily. Leather-soled boots are traditional, sharp and classy, and they will also mould to the shape of your foot over time. However, they won’t last as long as a decent rubber sole and might let in water if you’re spending the entire day cavorting through puddles (a likelihood with our infamous weather).
And what is Goodyear welted, you ask? A very good weather-proofing thing. A Goodyear welt is a thin strip of leather that’s sewn to the bottom edge of the shoe’s upper. The sole is then stitched to the welt, as opposed to directly to the upper. The result is a more durable and weatherproof shoe, with the added bonus that the sole is easier to replace in years to come without damaging the upper.
Whether you want a classic boot to withstand the ravages of time, a rock-god pair of dazzlers or a modern hipster hybrid, read on to discover your perfect Chelsea boots.
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Barbour Farsley Boot
Best for: town and country
People tend have a certain image of Barbour. Surely it’s what Prince Charles wears while trundling through the thickets on his Highgrove estate. It’s for horsey rural types. HRH may well do so, but this veteran best of British brand from North Shields has been embraced more and more by city folk this century, as well as collaborating with designers like Alexa Chung. And it’s not posh prices either. We love the Farsley boot, an affordable, contemporary update on classic Barbour style that suits both the Cotswolds and Clapton. It has the brand’s iconic ‘walking man’ pattern on the rubber sole, a natty canvas detail running down the back and the rough-textured suede is quite gorgeous. We rather like our new rustic-urban crossover look.
Buy now £112.49, Zalando
Dr Martens 2976 Smooth Clash Boot
Best for: downtown funk
A gigantic pair of chunky street-stompers is the way to give attitude, right?
Well, not always – sometimes a blast of contrast is all you need, and Dr Martens’ eye-popping Clash boots do just that. Made from smooth leather in black and industrial grey with ultra-bold yellow stitching, they strike a proper, punchy urban pose.
Stiff to start with, the smooth leather will relax and it’s superbly tough. The moshpit or a bout of parkour is no problem for these heavyweights.
Expect all the comfort and reliability of classic Dr Martens and those famous bouncing soles, and while you might not imagine so for the reasonable price, these are Goodyear-welted too. The only DMs worth sliding into.
Buy now £149.00, Dr Martens
Grenson Sneaker 52 Boot
Best for: hybrid comfort
Grenson, a Northampton stalwart of very fine footwear for 156 years, has dreamt up this decidedly non-traditional Chelsea/duck/sneaker hybrid - yes, three boots in one! But it’s also quirky simplicity at its best.
Made from a single piece of rubberised calf leather, it features elegant duck-style stitching on the toes (none of that moulded nonsense) and a contrasting soft suede ankle cover.
Besides looking fabulous, it’s extremely light, totally waterproof and we love the deep, wide sole which feels like a mini-mattress underfoot. Once on, we really didn’t want to take these off – if your feet are getting an all-day cuddle, why on earth would you?
Buy now £275.00, Grenson
Russell & Bromley Beechwood Boot
Best for: a touch of urbane polish
You’re refined, you’ve got an invite to the ambassador’s reception (okay, cousin Maisie’s wedding) and you’ll be decked in your finest tailoring. The finishing touch? This elegant take on the classic Chelsea boot.
Crafted in Tuscany from hand-selected calf leather, the Beechwood is a slick, slimline beauty. The supple upper is a gorgeous mahogany tone, while the leather sole will suit traditionalists, with the added benefit of being overlaid with rubber for extra durability and grip.
Even straight from the box, these are snug and gentle on the feet, ready for you to fix up and look sharp. Can’t stand the brown boots and suit combo? No worries, they also come in black too.
Buy now £275.00, Russell & Bromley
Tricker’s Henry Country Dealer Boot
Best for: your classic forever boot
Say hello to the Rolls-Royce – nay, the Lennon and McCartney – of boots.
Tricker’s, one of the Northampton elite, is England’s oldest shoemaker and anything they produce is a guaranteed stone cold classic.
These beefy brogue-style boots are mightily solid, with super-tough commando soles that aren’t just Goodyear, but storm welted too. Although downright imposing (possibly not the choice for a dainty dandy look), they mould to the feet and ankles perfectly – and we love the rich espresso leather.
If you wince at the price, believe us when we say they’re the best value boot here. We’ve done the sums: they might cost four times as much as a standard boot, but they’ll probably last ten times as long, and even then you can send them back to Tricker’s to be remade almost as new. Basically, beautiful boots for life.
Buy now £495.00, Tricker’s
Church’s Bletsoe Suede Strap Sigar Boot
Best for: English heritage with a twist
If there’s one name in high quality British shoes that’s been lauded for centuries, it Church’s. The Italians liked them so much that these days the brand is part of the Prada Group.
Although best known for refined English elegance, we are rather beguiled by these Bletsoe boots that come with something of a modern twist – literally so with that ankle strap.
Besides that strap, it’s a classic boot, with a Goodyear-constructed diamond rubber sole (a subtle solution to offer extra grip) and leather heel. The suede is truly wonderful.
If you adore the classics but want a relaxed update, these are your new best friends.
Buy now £920.00, Church’s
Dune London Chai Boot
Best for: a casual classic on a budget
We’d all like to stomp around in swanky boots, but sometimes the bank says no. But that doesn’t matter; if your price range is pointing you to Dune London’s little runarounds, you’ll be a happy chappie once again.
With its pale rubber sole, these classic Chelsea boots have more than a hint of the beloved desert boot about them. Two birds with one stone for anyone who loves both styles. The navy suede upper is supple and feels reassuringly thick, while they are pretty cosy without having to be worn in.
And, although casual, we reckon you might be able to get away with pairing them with a suit too.
Buy now £90.00, Dune London
Loake Huxley and McCauley Boots
Best for: heritage excellence at a handsome price
For a pair of Chelsea’s steeped in centuries of noble Northamptonshire shoemaking without the faint-inducing price tag, look no further than Loake.
A family business for its 142 years, Loake makes fantastic footwear, and often at a fair price. We couldn’t decide between the Huxley and McCauley boots, both from the brand’s more contemporary ‘Design’ collection. Each has Goodyear welted soles (remember, that’s good) that offer a hugely satisfying amount of squish underfoot. They also fit like a soft, friendly glove to add to the instant comfort factor.
The McCauley’s tan nubuck upper is something of a tactile delight, but we’re even more taken by the Huxley’s gorgeously textural, hand-painted burgundy grain leather. Either way, for quality bang for your buck, you’ll be hard-pushed to beat these.
Buy now £199.00, Loake
RM Williams Santa Fe Boot
Best for: rock’n’roll ranchers
Wanna be more Jagger? It’s time to up your game – by two inches to be precise.
Forget any notions of scrimping on a weird budget version from your local Goth and Roll emporium and instead invest in these Cuban-heeled hellraisers from the best bootmaker in Australia.
Everything about these boots is sleek, understated yet somehow in your face at the same time. Crafted in Adelaide from a single piece of willow leather in the same way RM has been doing since 1932, these have that rare marriage of class and chutzpah oozing from every seam: from the brass-screwed leather sole to the square rodeo toe and flourish of decorative stitching.
They are tough enough for ‘hard work’, apparently, although we’d recommend getting off your horse and partying.
Buy now £375.00, RM Williams
Blundstone + Finisterre Boot
Best for: vegans
You’d have to have been hiding under a wombat for the past 152 years if you’ve never come across Blundstone.
The Tasmanian brand has become a byword for go-anywhere, suit-anyone boots. Whether you’re a Blundstone devotee or you fancy saving the planet and a few furry friends along the way, you might want to get your toes into these vegan babies.
A collab with Cornish surf and coastal wear label Finisterre, these look and act like good old Blundstones, so expect easy-going comfort and plenty of knockabout resilience. I also love the pop of green and bold yellow stitching on this version.
Now, credentials: just how vegan are they? 100 per cent, with lab certification that goes forensic: it searches for animal DNA in the upstream manufacturing process.
As for the material, well, you might find yourself exclaiming, “I can’t believe it’s not leather!”
Buy now £160.00, Finisterre
Jeffery-West Boots
Best for: when you wanna go full devil-may-care
Embrace the decadence with Jeffery-West, the master of turning the volume of your feet up to 11.
Founded in 1987, when it comes to craftsmanship this shoemaker is Northampton through and through – albeit with all the gloriousness of full-on rock’n’roll.
The brand’s Scarface and Dexter boots use gorgeous, hand-coloured leather and come with leather soles, while the pricier Dexter is also Goodyear-welted.
But just look at that sharp-as-Pacino Scarface boot! It could have so easily been over the top, but the lightning bolts give the perfect level of detail.
Jeffery-West boots are inspired by music and (anti) heroes, so the Dexter is named after our favourite TV blood-splatter analyst/serial killer, while the Scarface has a sax-blowing skeleton punched onto the sole. Not flamboyant enough? Check out the website for even wilder styles.
Buy now £285.00, Jeffery-West
