The Best Winter Boots Styles

Hiking Boots

Have you been spending your weekends training for a forthcoming trip up Kilimanjaro? If the answer’s no, then you can be forgiven for overlooking the humble hiking boot as a viable footwear option. But only just.

Regardless of your outdoorsy aspirations (or lack thereof), hardy hiking boots have established themselves as foul-weather footwear essentials over the past few years – especially among sharp men who prize a shoe’s ability to face down all manner of meteorological nasties in style.

We’re not experts in adventure sports, so we’ll leave recommending boots for seriously tough terrain to the professionals. What we can do, though, is suggest designs that are ideal for navigating city streets, heavy dog walking sessions and the occasional trip to a countryside pub.

You need a pair that offers untold levels of comfort, ankle support and other orthopaedic box-ticking features such as full-leather linings and cushioned footbeds. (Although you could sack that off and get a beautiful but hardly practical suede pair from a high-fashion designer that hasn’t seen a mountain in their lives.)

Team them with other tough-as-old-boots menswear staples like raw denim, corduroy, twill or flannel shirts and cable knit jumpers. You could also pair them with rainstoppers and fleece to lean fully into the outdoors trend. Or be bold and use them as a striking counterpoint to tailoring – just not for your next job interview.

Brogue Boots

If you’re not ready to go full Bear Grylls with a pair of hiking boots, there are other, subtler ways to infuse your winter look with some outdoorsy influences. A sartorial hybrid, the brogue boot comes with the same reassuring weight and solid construction of hiking boots, but with all the wing-tipped, country-manor smartness of brogues.

As a general rule of thumb, you can wear your brogue boots with any outfit you might normally wear with traditional brogues, so lace up a dark brown or black leather pair with heavier wool suiting, and smart trouser and shirt/cardigan combinations.

However, owing to their winter-readiness, brogue boots also play well with pieces that straddle the rugged-refined divide, such as heavy-gauge knitwear, gilets, waxed and quilted jackets, as well as heritage fabrics such as corduroy and tweed.

While sock-flashing isn’t necessarily frowned upon when wearing a pair of these, it’s not an entirely natural fit with the brogue boot’s finesse either. Stick instead with trousers with a neat break (i.e. that finish around the top set of lace eyelets), or roll more casual trousers and jeans up to the same point for a smart finish.

 

Work Boots

Some of the best boots ever made were first designed decades ago for people to wear in factories and shipping yards. The steel toe caps may not have survived the fashion crossover, but many other features have: waterproof materials, padded ankles, high-grip soles and cosy linings. Why wouldn’t you want those things for your feet when it’s freezing outside?

The most iconic work boots – the Timberland Yellow Boot, Red Wing’s classic moc toe – have remained almost unchanged for decades, which makes it surprising that they’ve been adopted by such diverse style tribes. Hip-hop artists, lumbersexuals and workwear enthusiasts all love a work boot.

That means you can pair them with a range of casual (always casual) outfits, from joggers to jeans, trucker jackets to parkas. Look for dyed leather or waterproof nubuck and sealed seams to keep the puddles at bay.

 

Combat-Style Boots

 

Like most items in a man’s wardrobe, boots have a proud history of military service. From high lace-ups designed to keep out trench foot to modern tactical designs, combat boots have recorded a number of victories on the fashion front.

Right now, they’ve not just won the battles, they’ve won the warcore. The directional trend for combat trousers, holsters and all things military means there’s rarely been a better time to buy this style. Not that you have to leave the house looking like a character from Call of Duty.

Look at Ryan Gosling’s character in Blade Runner 2049. He paired tactical boots you can buy on Amazon with a statement overcoat. Or designer Charlie Caseley-Hayford who wears his trademark high boots with classic tailoring. Streetwear fans might pair them with jeans and a bomber. Or an easy middle-ground is heritage wear: wool, twill cotton, generous fits and plenty of herringbone.