Over Christmas, at my other half’s behest, I tackled the black-and-brown leather Jenga tower of old boots in the cupboard under the stairs. I’ve always preferred boots to shoes — an ankle boot says more about its owner than your average loafer or lace-up — but even I, hapless hoarder and style obsessive, could admit that the 15 or so pairs stacked precariously around the boiler felt unnecessary. The task of distilling my erstwhile collection was made just about palatable by my most recent acquisition, a pair of John Lobb’s Lawry boots in polished black calf. To me, they’re the epitome of timeless Chelsea boots; beautifully made with elegant almond-shaped toes (neither too round, nor too pointed), a sweeping line through the boot’s waist into close-fitting heels, and a quality of leather that stands up to the simplest of silhouettes.
I’ve found them so useful they have convinced me to let go of the majority of my stockpile — a true New Year’s miracle. With 2023 marching on, it’s as good a time as any to think about your own footwear refresh. If, like me, you need “one pair that’ll do everything”, Chelsea boots are a sensible starting point — easy to wear with either tailoring or casual pieces. Don’t just take my word for it, either. Chelseas are the go-to of MatchesFashion’s head of menswear, Damien Paul.
“I love a modern Chelsea, particularly with a bit of heel from brands like Lemaire,” he says. “It’s an extremely versatile boot — you can easily take it from day to evening.” I tend to wear mine with wide-leg, pleated trousers in heavy brushed cotton or corduroy, finished with generous turn-ups. Hung neatly at the hems with no break, they look clean styled with a cashmere sweater and suede blouson. Alternatively, they can be smartened up with a flannel button-down and unstructured double-breasted jacket (this season’s Games blazers from Drake’s are worth a look).
For me, a boot without a Cuban heel feels pedestrian right now Photographer James Harvey-Kelly While John Lobb’s are unashamedly classical, Chelseas from the likes of Tod’s, Loewe and Prada present a chunkier, fashion-forward silhouette — feeding into a trend that’s been gathering speed in recent years. “We’re seeing a shift in customers connecting with fashion interpretations of [footwear] classics,” Paul confirms. “Heavy boots lend a forward-facing attitude to a pared-back outfit.” Even old-school shoemakers have been getting in on the action. Crockett & Jones, the 144-year-old manufacturer that produces 2,500 pairs of shoes a week in its Northampton factory, specialises in robust yet good-looking boots. The brand introduced three pairs of chunky boots with cleated rubber soles in 2018, and now has 24 models available.
Sales of heavy-soled boots increased 170 per cent between 2021 and 2022, the company says. “Consumers are buying these types of boots for their quality and their chunky look and feel,” says Crockett & Jones brand director James Fox, dialling in from the company’s HQ. “This chunkier style is quite casual for a Goodyear Welted shoemaker like us . . . but it’s still a heritage look. Our original rubber sole dates back more than 100 years.” Classic leather ankle boots paired up with straight-leg jeans on the streets of Paris . . . © Getty Images . . . and a more fashion-forward silhouette worn with cropped checkered trousers © Getty Images The company’s rugged Coniston Derby boots, Islay brogue boots and Chelsea 11s in Scotch Grain leather all feature thick rubber soles. Treat them as dependable weekenders and pair with neatly tapered chinos, cords or washed denim. Thick knitted socks and a well-worn chore coat complete the look.
Rolled-up hems work nicely with casual boots like these, too — and draw the eye to your fancy footwear. There’s also scope to have fun with the size of your heels. Smart, 1970s-style Cuban-heeled boots have been creeping back into vogue for men, care of brands such as Saint Laurent and Celine. To photographer James Harvey-Kelly, who lives in RM Williams’s block-heeled Yearling boots, they’re not something to be afraid of. “For me, a boot without a Cuban heel feels pedestrian right now,” he says. “I first bought mine as a bit of a ‘let’s see’ kind of purchase, and I’ve not worn any other boots since.” Unlike a cowboy boot (which even I would struggle to wear) this new breed of slightly retro rock-aristocratic ankle boots are surprisingly low-key — perfect with dark tailored trousers cut with a slight taper and cropped hems, a tweedy raglan coat and cosy sweater for a slinky, Bohemian look. Of course, there’s an art to pairing boots with tailored pieces.
Disgraced Australian financier Lex Greensill has a penchant for wearing expensive two-piece suits with rugged RM Williams boots — this is the sartorial equivalent of finishing a sole meunière with a jar of Texas Pete’s Hotter Hot Sauce. To get suits with boots right, take your lead from the style icons of yesteryear, says Parisian tailor Nicolas Gabard, whose brand Husbands offers a masterclass in sophisticated suiting. Margiela’s Tabi boots add a subtle eccentric touch to a classic outfit . . . © Getty Images . . . while styles with chunky rubber soles offer a modern alternative to classic options © Getty Images “Not all boots work with suits. We’re talking about the kinds of chukka or Chelsea boot styles worn by The Beatles, The Stones, Brian Ferry — they help you to feel sexier and more confident, and add a new dimension to a suit,” he says. Take a look at how Husbands mixes tailoring with its Italian-made ankle boots and you’ll get the drift. Charcoal chalkstripe or bold Prince-of-Wales check suits with wide lapels and high-waisted trousers are finished with polished black boots, while sporty tweed jackets are layered over cashmere rollnecks and slim white jeans, with Cuban heels poking out beneath.
It’s a quintessentially Parisian take on suiting and booting, but it works brilliantly. John Lobb Lawry chelsea boot, £1,495, johnlobb.com Celine Homme suede boot, £830, celine.com If you’re in the mood to channel your inner Alain Delon, invest in a pair of Husbands’ crackled patent leather buckle boots, which look like they’ve stepped straight out of the ’70s. “Of course, you’re wearing something unexpected with boots like these, but that’s the point. Style involves taking risks,” Gabard concludes. But what if you’re a sneakerhead? Is there a pair of boots out there for you too? Absolutely, says Adam Lewenhaupt, founder of Swedish sneaker brand CQP, which released a range of technical sneaker-boot hybrids in October. “I think that for anyone who wears sneakers, this kind of boot is natural to turn to right now,” he explains. “They are highly functional, but bring a certain coolness to bear if done and worn right. Technical footwear, matched to more classic and non-technical outerwear, is an interesting juxtaposition of styles.
Vibram meets cashmere, if you will.” Cuban-heeled boots for men are back on the runway at Celine © Alberto Maddaloni Of course, the bravest among you could take the idea of juxtaposition a step further. Designer and founder of menswear label LEJ Luke Walker is a passionate advocate of Maison Margiela’s Tabi boots, with their divisive hoof-like silhouette. The design is inspired by a Japanese walking sock of the same name, and makes quite the fashion statement. “I don’t like dressing as a single character — whether that’s a guy in a suit, or in some sportswear — I like to mix it up,” Walker says. “Like classic boots, Tabis are well made, in good materials, but there’s something that’s slightly ‘other’ in the design. At a distance, you’re just wearing a pair of black boots, but up close they have a really different silhouette that stands out.”
Selecting your own perfect pair of boots is of course a very personal decision, like choosing boxers over briefs, or finding the right hairdresser. Whether you consider my late lamented footwear hoard mildly amusing or (as my partner likes to tell me) faintly unhinged, there’s no denying that good boots — like any other piece of the wardrobe — can be tools to express a part of your personality. Yes, they should be functional, but boots can be fun too. And, at the risk of sounding like your mother, you can tell a lot about a man from his proliferating boot collection.