Summer has been problematic. One day we’re strutting into the office, pleased as punch with our weekend tan top-up. The next, we have to fake a Monday morning smile as we squelch through reception. Unfortunately, now autumn’s arrived, you’re going to be dealing with the latter more than the former.

While we can’t offer much weather-wise, we can solve the wet sock scenario.

“Many people continue with their summer kicks well into autumn and winter and then wonder why they’re not weather-repellent,” says stylist Jenna Riddle. “Instead, the rainy season should entail a completely new footwear wardrobe.”

And according to Riddle, thick soles work better if you want to trounce pavement puddles. “Nothing can beat solid, well-stitched leather fabric-wise,” she says. But rubber and Gore-Tex hybrids come close.

Pepe Jeans Barley Chukka Boots

Chukka boots are underrated. Not only do they sit perfectly with rolled up jeans and dressed-down tailoring, they’ll also handle soggy weather thanks to tight, leather construction (well, so long as you don’t go for suede).

Better yet, Pepe Jeans has thrown in a thick yet lightweight rubber sole for increased traction and comfort.

Available at Pepe Jeans, priced £115.

Pepe Jeans Barley Chuka Boots

Ted Baker TTANUM3 Leather Brogues

Thick Vibram soles strike the perfect chord between traditional and trend-led. But what if the event calls for classic kicks only?

Look for watertight leather on the upper and a slimline rubber sole. It looks smart from above but will handle anything wet below.

Available at Ted Baker, priced £150.

Ted Baker TTANUM3 Leather Brogues

Dr. Marten’s Whiton Reflective Boots

Autumn brings rain. And early evenings. If there’s no office dress code and you prefer a bicycle over National Rail, the Dr. Marten’s Whiton boot combines the brand’s signature design with a light-reflective coating.

Perfect if you want to keep dry (and alive) on the commute.

Available at Dr Marten’s, priced £105.

Dr Marten’s Whiton Reflective Boots

Clarks Originals x Horween Leather Co. Desert Boots

Sneakers always get the collab treatment. Sensible leather footwear? Not so much. Refreshing, then, that Clarks Originals teamed up with Horween Leather Co, the US’s oldest running tannery, for a pair of desert boots more suited to the damp.

Available at End Clothing, priced £119.

Clarks Originals x Horween Leather Co. Desert Boots

Barbour Cullercoats Chelsea Boots

The great outdoors needn’t mean sprawling estates and pheasant shooting. Instead, Barbour creates functional, rural designs that work in the city too. So you can wear them with your waxed jacket on the estate, or a parka in town.

Available at Barbour, priced £139.

Barbour Cullercoats Chelsea Boots

Hunter Original Side Adjustable Wellington Boots

When the term ‘downpour’ doesn’t quite cover the flash flood on your doorstep, rubber-soled shoes should be nixed for something heavy duty. Like Hunter’s classic adjustable wellington boots, which won’t just traverse a popped drain, but also double-up for the festival run.

Available at Hunter, priced £100.

Hunter Original Side Adjustable Wellington Boots

Grenson Sharp Leather Brogue Boots

There’s merit in heritage apparel. But what to wear when you find purpose-built features unsightly?

These leather brogue boots from Grenson combine Savile Row-worthy aesthetics with an ankle-high silhouette, so you’re not shaking puddles out of your shoes.

Available at Mr Porter, priced £225.

Grenson Sharp Leather Brogue Boots

Air Max 90 Mid Winter Trainers

For some, nothing but a sneaker will do. Those people are called sneakerheads. And when limited edition woven Mayflys succumb to showers, the Air Max 90 sneakerboots take the throne in all their hi-topped, ripstop nylon, weatherproofed glory.

Available at Footasylum, priced £124.99.

Air Max 90 Mid Winter Trainers

Tricker’s Toe Cap Dainite Lace Up Boots

Leather soles are smarter. But Dainite soles are smarter in the academic sense. This studded rubber is the same width as leather but completely waterproof, so you look as dressed up, but won’t fall down on wet marble floors.

Available at Coggles, priced £385.

Tricker’s Men’s Toe Cap Dainite Lace Up Boots

Jones Bootmaker Artillery Casual

If your workplace toes the smart-casual line, boots aren’t always office appropriate. Which means you need shoes that can handle and the boss’ dress code.

Jones’ Artillery Casual combines a traditional Derby upper with a thick, rubber sole – no raised eyebrows or damp toes.

Available at Jones Bootmaker, priced £69.

Jones Bootmaker Artillery Casual