best autumn boots
Dominic Cooper shot by Charlie Gray for Gentleman's Journal

The boots to see you through winter in style

Fuss-free aesthetics and unrivalled practicality make the humble leather boot a must-have this season

Although smart sneakers and sandals have been mainstays in our summer wardrobe staples, as the mercury drops and the nights draw in, only robust footwear will do. And, for something that’s guaranteed to protect your feet against the more challenging elements, you can’t go wrong with a pair of quality leather boots, and it pays to invest in the best.

With this in mind, we’ve compiled a list of the best boots to pull on and lace up this season, which promise to take you seamlessly (and stylishly) from the office to after-work drinks. Perfect for the gentleman who works as hard as he plays.

Crockett & Jones Coniston Boot

Crockett & Jones Coniston Boot

We make no secret of the fact that we are enormous fans of heritage shoemaker Crockett & Jones — one of the leading brands for hard-wearing, stylish, lace-ups. One of its most popular silhouettes is the Coniston, and it’s not difficult to see why. Designed as a higher leg derby with a straight toe cap, this boot combines practicality — thanks to a storm welt that prevents water seeping into the upper — with a sleek, heritage design.

Crockett & Jones Coniston Boot

Coniston Dark Brown Scotch Country Grain

£470

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Church’s Wootton Leather Lace-Up Boots

Church’s Wootton Leather Lace-Up Boots

A simple, rugged lace-up boot, the Wootton has a militant feel that calls for an autumnal combination of distressed jeans and leather jackets. Metal eyelets and natural calf leather enhance its tough attitude, as do its hardy cotton laces and practical pull tab.

Constructed on Church’s 81 last, it shares its shape with some of Church’s most traditional items and has an open-laced derby build that accommodates wider feet. Proving that it’s as utilitarian as it looks, it features a storm welt to help keep water out and a ‘Church & Co’ rubber sole for added traction.

Church’s Wootton Leather Lace-Up Boots

Wootton Calf Leather Lace-Up Boot

£495

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Common Projects Suede Chelsea Boots

Common Projects Suede Chelsea Boots

New York-based Common Projects combines utilitarian design with Italian quality and construction, resulting in a sleek, clean-lined aesthetic. Known for its cult-favourite sneakers, it’s applied its effortlessly cool aesthetic to this pair of chic suede Chelsea boots.

Understated, smart and designed with comfortably tapered toes, the shoes are set on cushioned rubber-crepe soles in a tonal hue and feature the brand’s signature embossed gold serial numbers.

Common Projects Suede Chelsea Boots

Common Projects Suede Chelsea Boots

£375

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John Lobb Grove Suede Chukka Boots

John Lobb Grove Suede Chukka Boots

John Lobb has produced the finest men’s shoes and boots since 1849. The shoes are still handmade the traditional way, with 190 steps and several weeks involved in the production of each pair.

These handsome chukka boots are crafted from soft suede and set on comfortable, durable rubber soles. A versatile choice, this classic brown pair is finished with sleek leather trims — and promise to keep you looking smart enough for work, without causing any uncomfortable rubbing.

John Lobb Grove Suede Chukka Boots

John Lobb Grove Suede Chukka Boots

£1030

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Cheaney Godfrey Leather Chelsea Boots

Cheaney Godfrey Leather Chelsea Boots

Cheaney’s black ‘Godfrey’ Chelsea boots are a lasting wardrobe investment, owing to the timeless design and superior construction methods used to craft them. This handmade pair has supple leather uppers that comfortably mould to the shape of your feet with wear and is set on Goodyear-welted soles panelled with rubber for enhanced durability. They’re thoughtfully detailed with pull tabs and elasticated sides to ensure you can comfortably slip them on and off.

Cheaney Godfrey Leather Chelsea Boots

Cheaney Godfrey Leather Chelsea Boots

£375

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UGG Harkland Boots

The boots to see you through winter in style

That’s right — them of the boots. But these hard-wearing, tough-talking kicks are a little more reliable than the UGGs of old. With state-of-the-art Vibram outsoles and more cushioning than even the most seasoned of hikers needs, the Harkland boots are a wintry spin on the suede hybrid style.

What’s more, they’ve been pretreated to repel moisture and stains, feature a 10mm wool lining woven from UGG’s own terribly soft textile and come in a handsome chestnut brown.

Looking for more autumnal style advice? Take a look at our favourite bomber jackets…

Further Reading