Chukka-ing It Down

The wet weather commute poses a conundrum. Do you opt for rainproof shoes and sacrifice style for dry socks? Or is squelching through the morning worth not trying to pair a suit and galoshes? Ponder no more, thanks to this chukka, from Reiss’ collaboration with US shoemaker Allen Edmonds.

It’s crafted from cordovan leather, which isn’t impregnated with the holes that turn your ordinary office shoes into puddle sponges. Just stuff with newspaper overnight so they keep their shape as they dry, and give them at least 48 hours between soakings.

Allen Edmonds Dundee Chukka Boot, available at Reiss, priced £495.

Allen Edmonds Dundee Chukka Boot

Crepe Protect

Wear leather-bottomed shoes in the wet and you’ll have to hit up your cobbler twice as often, since the sole softens up and gets shredded by pavements.

These Chelsea boots come strapped to crepe instead, which means no swollen cowskin, and no leaving flakes of it all over the office. Pair with your suit and a trench coat to be prepared for the unpredictable.

Black Chelsea Boots, available at Burton, priced £35.

Burton Black Chelsea Boots

Sole Survivor

The more indents your sole boasts, the less the likelihood of you ending up on your posterior when it’s slippy. But that surefootedness normally means formality takes a tumble instead.

Magnanni’s burnished lace-ups boast an embossed commando sole, which keeps you upright but – from most angles – looks flat. So you can rock them to work, even if your frontline is a computer monitor, not a warzone.

Magnanni Marcelo Lace-Up Boot, available at Harrods, priced £270.

Magnanni Marcelo lace-up boot

Suede In The Water

Most men will tell you that suede doesn’t wear well in winter. Untrue. Its nap – that’s the raised fibres that give suede its buttery texture – trap air, keeping your toes snug when it’s subzero.

The material is less pally with the wet, as anyone who’s seen their new shoes spoiled by an unsteady wine hand can attest. Which is why preparation is all: a weather app and a regular spritz of suede protector (£10.18, Amazon) should avert most mishaps. If disaster still strikes, you can buff out stains with stale bread crusts.

The Chelsea, available at Fairfax and Favour, priced £185.

The Chelsea Boot

Green Means Walk

It feels like we say this every year, but military green is trending. For those who still see winter as a time when only black and navy will suffice, ASOS’ heavy-duty boots update your look while still keeping everything else monochrome.

The commando sole will also take anything from snow to wet marble in its stride. Because nothing destroys your street goth sangfroid like taking a tumble.

Lace-Up Boots In Khaki Nubuck, available at ASOS, priced £50.

ASOS Lace Up Boot

Feet Heat

There are boots you slip into when the weather calls for long sleeves. And there’s the footwear you call on when snow necessitates digging your way to work. Even if the latter is less regular, everything about these hikers – from the Vibram sole that’s 30 per cent lighter than rubber but strong enough to cope with life-threatening terrain, to the waterproof nubuck upper, or the shearling lining that’s like slipping your feet into a duvet – is your insurance against whatever climate change brings.

Diemme Roccia Vet, available at Luisa Via Roma, priced £312.

Light As Air

Nike’s gift to the boxfresh obsessive who won’t leave the house after October, the sneakerboot is, as its name suggests, a hybrid of trainer and hiker built to boss wet streets.

Here, the flyknit upper gets a waterproofing treatment – keeping your kicks light without risking frostbite – and comes with reflective panels so you don’t end up under a car whose driver didn’t spot your steeze. The risks of that all-black look.

Nike Flyknit Chukka, available at Harrods, priced £150.

Nike Flyknit Chukka

Quack Addict

In the US, the duck boot is a prepster staple, adopted by Maine’s blue bloods the minute the snows roll in. Here, the weather tends more towards slush than blanketing. But that doesn’t mean you can’t adopt the look, tucking your drill chinos into a hiking sock then letting the rubber-coated upper pay heed to puddles, so you don’t have to.

Sorel Cheyanne Boots, available at Mr Porter, priced £110.

Sorel Cheyanne Boots