These leather boots will see you through winter in style

From hiking-influenced designs handcrafted in Northampton to a pair of sleek, sturdy Italian shoes, these are the best boots in which to tackle 2021

2020 wasn’t a vintage year, was it? That’s why, now we’ve finally made it out, we’re heading into 2021 as fast as our feet will carry us. But with all this wintry weather, that’s easier said than done. There are still icy spots, deep puddles and rough patches (both real and metaphorical) to contend with — and we’ll have to be tough as old boots to make it through. 

Or new boots, come to that. With the colder weather comes new collections — and we’ve found the perfect winter footwear to negotiate the end of a particularly unsteady year. That means big, chunky soles to tackle all terrains. It means rough and rugged leather to protect our every step. And it means soft, cosy linings — because couldn’t we all do with a touch of comfort right now? 

Cheaney Ingleborough B Hiker Boots

If you’re looking for a pair of sturdy-but-stylish boots for the New Year, Cheaney’s new ‘Ingleborough B’ design ticks every box. Handcrafted in the brand’s Northamptonshire factory, they’ve been created using Chromexcel leather — and benefit from reliable Goodyear welts and Brit Grip rubber soles. With lace-up front fastenings, they’re also one of several pairs we’re pulling on this winter that have traditional hiking boot influences. 

These leather boots will see you through winter in style

Cheaney Ingleborough B Hiker Boot

£395

Buy Now

Church’s Eastrock Monteria Calf Mountain Boots

Another recent example of the hiking boot aesthetic is the bold new ‘Eastrock’ design from Church’s. Burnished to a deep black finish with bold red ripcords of laces, they’re as ready for summits as they are for the streets. The best part? That lightweight ‘St Moritz’ soles — internally lined and with a contrasting colour mid-sole for a striking silhouette. 

These leather boots will see you through winter in style

Church’s Eastrock Boots

£640

Buy Now

Edward Green Connemara Boots

Inspired by Edward Green’s traditional ‘Galway’ design, these new ‘Connemara’ boots are also subtly styled to resemble classic hiking shoes — kitted out with storm welts and ski hooks. With a signature chevron pattern and padded ankle collar cut into the beautifully tanned, dark brown Delapré leather, they stand on rugged ridgeway soles — for even the most ambitious wintertime walks. 

These leather boots will see you through winter in style

Edward Green Connemara Boots

£1,265

Buy Now

Crockett & Jones Ross Boots in Fawn Suede

Crockett & Jones has stomped in a different direction. And the heritage British brand — which built the sturdy-soled boots that Shackleton wore on his Antarctic expedition — has outdone itself yet again with a new, hardy suede take on its ‘Ross’ style. On lightweight rubber soles, the boots may not look as hardy as the other tough, tanned offerings on this list — but they’re crafted from the strongest suede you’re ever likely to lace up. 

These leather boots will see you through winter in style

Crockett & Jones Ross Boots

£450

Buy Now

Tod’s Brown Leather Ankle Boots

But it’s not all Goodyear welts and stiff upper lips — Italian brand Tod’s new pair of leather ankle boots offer an alternative winter style. Gently brogued and semi-glossy, they’re as ready as the rest to stamp out the last disappointing weeks of this lockdown as the rest; but with elastic side panels, metal buckles and embossed pebble outsoles. 

These leather boots will see you through winter in style

Tod’s Leather Ankle Boots

£366

Buy Now

Looking for more quality leather goods? Past Vintage is the modern brand reviving traditional craftsmanship…

Become a Gentleman’s Journal member. Find out more here.

Further Reading