Step from weekday to weekend with these versatile shoe styles

Joseph Cheaney & Sons has been handcrafting fine footwear for decades. We turn to the heritage shoemaker to help with our workwear wardrobes.

Perfecting a work wardrobe can be a lot of, well, work. No longer required to wear shirts and suits to the office, we’ve loosened both our ties and dress codes to such an extent that we now begin every day standing startled in front of an open wardrobe. How casual is too casual? Should I still smarten up for meetings? What shoes give off the right image?

It’s a tricky business, this business dressing. But we can help — at least with one of those problems. Office appropriate footwear has always been something of a fine line to walk, but Joseph Cheaney & Sons — the Northamptonshire-based, handcrafted heritage brand — has been working hard on cracking the problem. With designs from Derby shoes to Chukka boots, the shoemaker offers versatile, unstuffy styles that are smart enough to wear throughout the working week — but also over the weekend. Take a look.

A textured Derby blends casual and formal styles

The Derby shoe is a great place to start. First designed as a popular sporting and hunting shoe in the 1850s, the style has stepped inside of late — erring on the formal side of footwear. But there’s something adaptable about these all-rounders, and Cheaney’s take on the style makes them the perfect shoes to take you from the week to the weekend.

The Deal II R Derby style comes with a full leather insole and Goodyear welts, not to mention a hugely hardy Double Dainite Rubber Sole. With an open lacing system and similar construction from mahogany grain leather, the Tenterden II capped brogue Derby shoes are also a good bet; bridging the gap between casual and formal in leather-lined style. Or, for a little more texture, the Horsforth EF shoes are a step in a more suedey direction.

Deal II R Derby in Mahogany

Deal II R Derby in Mahogany

£380

Buy Now
Horsforth EF Derby in Bitter Chocolate

Horsforth EF Derby in Bitter Chocolate

£380

Buy Now
Tenterden II Capped Derby Brogue

Tenterden II Capped Derby Brogue

£380

Buy Now

Boots are a rough, tough way to make an impression

A surefire way to lace a little more informality into your office outfit is to pull on a pair of boots. They’re rugged, yet refined — the ideal tonic to a starched suit and tie. And your options are many; from the Chukka — a boot with both sporting and military origins, to the Derby boot — typically considered a little more casual than a brogue boot.

Cheaney is the place to go for a Chukka. The brand’s Garforth design is the pinnacle of this smart-casual, low-ankle style — with our picks being the Bitter Chocolate Suede and Rustic Brown Calf colourways. Or there’s always the Sutton, with an open-lacing system, Goodyear welted leather sole and quarter rubber tip. Higher on the ankle, these are the perfect shoes to hop from the office to off-duty.

Garforth Chukka Boot in Bitter Chocolate

Garforth Chukka Boot in Bitter Chocolate

£380

Buy Now
Sutton Derby Boot in Khaki Suede

Sutton Derby Boot in Khaki Suede

£380

Buy Now
Garforth Chukka Boot in Rustic Brown Calf Suede

Garforth Chukka Boot in Rustic Brown Calf Suede

£380

Buy Now

A heavy-soled shoe combines casual capability and office-ready

Nothing says casual like capability — and shoes rarely come more capable than those with Goodyear Commando rubber soles. Chunky, hardy and oversized, Cheaney has taken these typically outdoor soles and heels and married them to smarter styles — reinventing the Derby, Brogue and Chelsea Boot with a fresh, utilitarian spin.

Just look at these Tamar C boots; handcrafted examples of bold country style ready to make an impression in the office. Or the Cairngorm II R Derby Veldtschoen shoes — with a bellows tongue, full leather insole and striking burgundy colour for extra impact. Alternatively, the Avon C Wingcap design take a conservative upper style and supersizes it with the chunky sole; a mixed-up mash-up of forms guaranteed to turn heads in the boardroom.

Tamar C Chelsea Boot

Tamar C Chelsea Boot

£395

Buy Now
Cairngorm II R Country Derby Veldtschoen

Cairngorm II R Country Derby Veldtschoen

£385

Buy Now
Avon C Wingcap Derby Brogue

Avon C Wingcap Derby Brogue

£385

Buy Now

Looking for a pair of more casual kicks? These are the best leather sneakers for winter…

Join the Gentleman’s Journal Clubhouse here.

Become a Gentleman’s Journal Member?

Become a Gentleman’s Journal Member?

Like the Gentleman’s Journal? Why not join the Clubhouse, a special kind of private club where members receive offers and experiences from hand-picked, premium brands. You will also receive invites to exclusive events, the quarterly print magazine delivered directly to your door and your own membership card.

Click here to find out more

Further reading