Army-style boots fit for marching into the office

These military boots are good to go anywhere – even to work. Aleks Cvetkovic reports

From left: Hermès calfskin Veo boots, £1,320. Paul Smith calfskin riding boots, £795. Bottega Veneta leather boots, £720. Ami leather Chelsea boots, £435
From left: Hermès calfskin Veo boots, £1,320. Paul Smith calfskin riding boots, £795. Bottega Veneta leather boots, £720. Ami leather Chelsea boots, £435

Boots with thick, sturdy soles have, historically, been the preserve of the honest working man. Designed with labourers in mind, heavy-duty lace-ups, often set on rubber commando soles, were first popularised in the early 20th century as a practical alternative to dress shoes. Today, though, robust-looking boots are gaining ground as a fashionable complement to suits and separates, with a new spate of styles shaking off their purely functional reputation.

“Heavy-duty boots with thick soles dominated the autumn/winter 2019 catwalks,” says David Morris, senior footwear buyer at Mr Porter. “When worn with suiting, they toughen up tailored pieces and bridge the gap between formal and casual style.”

Corneliani leather boots, £560
Corneliani leather boots, £560

There is no shortage of brands demonstrating just how this pairing works. Dior’s runway centred on elegant monochromatic tailoring styled with sleek yet sturdy boots. It has added oversized rubber soles to black leather Chelsea boots (£860) with a technical fabric trim, and black leather derbies (£930) with detachable gaiters and bout fleuri decoration on each toe cap. Bottega Veneta’s take on boots with suits is even more dramatic – for the house’s autumn/winter show, dark oversized tailoring and asymmetric overcoats were paired with high-rise boots (£720) set on thick soles. Luxury footwear has seldom looked more imposing.

Brunello Cucinelli is also contrasting tough with soft. The house’s thick-soled styles (£1,100) are more akin to mountain boots paired with sleek suits in cotton corduroy. “We have always tried to juxtapose formal with informal in our collections,” says Brunello’s daughter Carolina Cucinelli who works for the family business. “Although mountain boots are associated with the outdoors, ours are made with a soft shearling lining and cashmere laces, and are more than appropriate to wear with a suit.” Berluti is also taking cues from rugged hiking boots: its lace-up leather Brunico Bolzano style (£1,770) has dense, cleated rubber soles and is made in Berluti’s signature Venezia calfskin with a patinated finish, offering an elegant yet robust option to wear with the house’s refined suiting.

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A more buttoned-up take on the trend comes courtesy of Paul Smith, where models took to the runway in thick-soled, calf-length riding boots (£795) paired with tailoring and brightly coloured riding coats. While pulling on riding boots to pick up a pint of milk on Saturday morning in Hampstead or Highbury might sound a little outré, Paul Smith’s styles certainly demonstrate the breadth of the trend. If not a full suit, a tailored overcoat is lent extra swagger with the addition of chunky boots, especially when worn with a fine-merino rollneck or buttoned-up dress shirt beneath.

Other brands such as Paris-based Ami have pushed the trend in a different direction, using it to lend tailoring a retro rock ’n’ roll aesthetic. Throughout the 1950s and ’60s, subcultures such as the Mods wore Chelsea boots with slim tailoring – shunning conventional lace-ups for boots that represented youthful rebellion. Ami’s collection reflects this demeanour, with Cuban heels and sharply pointed toes set upon thick leather soles. Available in either glossy black or bright white leather, its Chelsea boots (£435) make natural companions to svelte slim‑cut suits. Similarly, Hermès’ winter range includes leather Veo boots (£1,320) designed with rubber soles, wraparound ankle buckles and a matte-lacquer finish for footwear with no small amount of attitude. 

Tod’s leather Chelsea boots, £498
Tod’s leather Chelsea boots, £498

Tod’s collection is big on rock-star boots too. Its Gommino cap Chelsea style (£498) takes the signature rubber studs that finish the brand’s Gommino driving shoes and transplants them onto highly polished Chelsea boots with double-thickness soles. These boots strike a balance between city and sports shoes. “We wanted to merge a material like leather with high-tech rubber to create a hybrid between these two different attitudes,” one of the design team tells me. Tod’s also has dark‑brown mountain boots (£510), which are just as hefty, set on inch‑thick soles with derby-style laces and punched-metal eyelets. 

Even Italian tailoring houses such as Corneliani are championing this subversive look. Corneliani’s collection layers smart overcoats and tailored trousers with boots (£560) set on chunky lugged-rubber soles. “Boots have become the perfect alternative to sneakers,” explains the house’s style director Stefano Gaudioso. “The edginess of commando soles mixed with tailoring is the perfect formal/informal combination.” 

From left: Crockett & Jones leather Chelsea boots, £465. Berluti calfskin Brunico Bolzano boots, £1,770
From left: Crockett & Jones leather Chelsea boots, £465. Berluti calfskin Brunico Bolzano boots, £1,770

Chunky boots have even made their way into heritage shoemaking. Crockett & Jones, whose 140-year‑old Northampton factory makes 2,500 pairs of Goodyear-welted shoes each week, released an experimental trio of men’s shoes last winter called The Black Editions, including a vaguely intimidating pair of black Chelsea boots made with Scotch-grain leather and set on Vibram-rubber soles. The boots were meant to be limited editions, but have proven so popular that Crockett & Jones has re-released them this season, and added a second version in dark‑brown Scotch-grain (both £465). “Our boot production has gone up significantly, thanks in part to the move towards rubber commando soles in mainstream fashion,” says the firm’s managing director Jonathan Jones. 

Elsewhere in the heritage-brand camp, Edward Green has also expanded its collection of work boot-inspired designs. Its new Cranleigh boot (£1,365) is designed with a derby lacing system, raised hand-stitched aprons and metal speed hooks for a sturdy look, and is set on lugged-rubber ridgeway soles. The boots are available in four colours, from black to burgundy, all made from a luxurious printed version of delapré calfskin, which is tanned in nine different oils. 

From left: Dior calfskin Chelsea boots, £860, and calfskin derbies with detachable gaiters, £930
From left: Dior calfskin Chelsea boots, £860, and calfskin derbies with detachable gaiters, £930

For a masterclass in how to wear the look, check out Charlie Casely-Hayford, a designer known for pairing his sleek tailoring with thick-soled, military-surplus styles. “Boots help to remove the stiffness from a suit and shift it into a new arena that feels carefree,” he says. Even so, to Casely-Hayford, this change in the work boot’s identity isn’t purely about playing with conventions. “Wearing boots like this offers more than just a contrast; it creates a strong aesthetic when something dainty won’t cut it. Boots are about durability and being active. They are a modern antidote to the classic shoe.”

Whether classic shoes require an antidote or not, elevated work boots are certainly having a moment – and helping to contemporise men’s tailoring while they’re at it. From the collections of international designer brands, to experiments by historic British shoemakers, humble, thick-soled boots have never looked so striking.

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