How to choose the perfect pair of men’s winter boots

Looking for a pair of boots to carry you through the cold, dark winter and beyond? Check out our ultimate guide to men’s leather boots. From sophisticated Chelsea boots, to heritage brogue boots, smart-casual chukkas, and winter-ready Cumbria boots, we’ll help you choose the best frosty-weather footwear for your needs. For extra guidance, take our quick boots quiz at the end of the article. 

Sophisticated Chelsea boots 

collection of chelsea boots from Samuel Windsor

Chelsea boots are always stylish
Image source: Chelsea boots from Samuel Windsor

Lend your workwear a touch of sophistication by showing up at the office suited and booted to perfection in black leather Chelsea boots. Sleek, slick, and always stylish, Chelsea boots are plenty smart enough for formal wear. A great choice for cooler weather, they keep your feet warm and dry without breaking formal dress codes.

Not wearing a suit? Go for the slightly less formal brown leather Chelseas with chinos. And those who work in people-facing jobs like teachers and counsellors will find that approachable brown suede Chelsea boots are just the ticket. Add a tweed jacket to smarten things up a notch.

Smart-casual boots for work 

collection of smart-casual boots from Samuel Windsor

From left to right: Oxford boot, monk boot and Fairfield boot
Image source: Leather boots from Samuel Windsor

Are you a member of the growing cohort for whom dressing in a suit for work is no longer the done thing? If so, you’ll want a pair of winter boots that’s up to the commute but which still looks great at the office, school, hospital, etc.

If you’re a wool-rich trousers, cotton shirt and cashmere jumper kind of guy, a pair of stylish monk boots should do the trick. While their origins are ecclesiastical, these days a pair of monks is not so much for men of the cloth as men who like to don their glad rags and step out in style.

If you head off to work in jeans or moleskins, try a pair of Fairfield or Oxford boots – they’re slightly more relaxed than Chelsea boots or monk boots, but still plenty smart enough for work. Both offer supreme comfort, tough commando-style soles and good ankle protection. Choose the Fairfield for a dressy-looking take on the brogue or, for a slightly more formal outfit go for the Oxford boot which is all about the heritage vibe.

Versatile brogue boots 

collection of brogue boots from Samuel Windsor

From left to right: Black leather country boot, tan leather country boot, tweed country boot
Image source: Samuel Windsor leather boots

Winter wedding? You’ll be looking for a classic tweed three piece suit, smart shirt, beautifully knotted tie, and a pair of stunning brogue country boots. A heritage look that’s never out of fashion, quality tweed keeps you wonderfully warm for blustery outdoor photos, while a pair of country boots keeps your feet snug while you pose for snaps and chat with the bride’s mother.

Brogue boots from Samuel Windsor feature hardwearing, non-slip rubber Goodyear welted soles, full ankle support, and a very attractive stacked heel. Smart enough to style up a tweed suit or jacket, these versatile brogue boots are also great for casual weekend wear or a night out with friends.

Stylish chukka boots

collection of chukka boots from Samuel Windsor

The sleek silhouette of chukka boots make them a versatile choice
Image source: Samuel Windsor Chukka boots

For casual footwear that doesn’t let the side down, you’ll need a boot that looks great with jeans, cords, moleskins, or chinos. You need something comfortable for knocking about in, yet smart enough for pub lunches and evenings out. A pair of chukkas is the perfect selection. You get a low ankle, sleek silhouette, and casual, three eyelet lacing which, paired with half-rubber Goodyear welted soles, gives you winter walking peace of mind.

Go for black boots to match black jeans and moleskins. Alternatively, black, brown, or suede all go well with your blue jeans. We particularly love suede chukka boots with cords, a Tattersall shirt and tweed jacket – a laid back look with a nod to the country life.

Practical winter boots 

collection of country boots from Samuel Windsor

From left to right: nubuck Chiltern boot, brown leather Chiltern boot, Cumbria boot
Image source: Leather boots from Samuel Windsor

Looking for something sturdy to beat the winter weather? A pair of prestige Chiltern boots makes a fine choice. Offering good grip, and coming in a choice of nubuck or brown leather, they provide excellent performance when the barometer takes a dip.

Wear these with jeans, cords or moleskins and top with plenty of layers – cotton t-shirt, flannel lumberjack shirt, warm jumper and perhaps an adventurer coat to finish off a look that’s great for running errands round town without letting your style credentials slip.

For a pair of tough winter boots that can take the worst of wet weather days, check out our prestige Cumbria boot. An excellent solution, these chunky, winter lace-ups offer excellent grip, fine Italian leather uppers and a cushioned inner to keep your feet comfortable whatever the terrain.

Pair your Cumbria boots with moleskins or jeans, brushed cotton shirt and rugged fisherman’s jumper. Top with a wax jacket and flat cap for a water resistant answer to the winter blues. These are no-nonsense boots for dog-walking gents who like to roam.

A good pair of boots keeps your feet warm and dry and prevents slips while you’re out and about. For a quick visual recap to help you make the best choice, take a look at Samuel Windsor’s essential guide to men’s boots infographic.



Posted in Leather boots.


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