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Your guide to winter boots

Your guide to winter boots

If you haven’t already, put those crisp white trainers to the back of your wardrobe – boot season is upon us once more. And to ensure you’re stomping in style this season, we’ve enlisted the help of menswear stylist and boot connoisseur Toby Standing to break down all the styles that are essential for this season and the next. From how to shop lace-up boots successfully to why suede boots do work for all sorts of weather, count this as your ultimate guide to winter boots. 

The workboots

As expected with some classic workboots, they’re extremely practical. These heavy-duty boots, with their signature eyelets and heftier lug sole are the perfect pair to reach for on those gloomy, rainy days where you need to combat the elements. 

This style does take inspiration from the older forms of hiking boots, so while they might not offer some fancy GORE-TEX lining, ultra ergonomic features of modern day styles, they will see you through pretty much anything less than a hike up a mountain – you know, winter walks, your commute, things like that. 

The lace-up boots

Photographed: Grenson DAWSON (£315)

There’s something about swapping out your usual leather shoe like a derby or brogue for a pair of lace-up boots that just feels so right in winter. The best part is you can find these in a whole manner of colours and materials. “I’m a fan of a suede boot in winter (I know, god forbid), but I think the texture really adds something to a look and you can keep them protected fairly easily after all,” Toby says. 

Toby suggests not going for any more than eight eyelets on a boot like this, otherwise it can end up looking a little costumey. As a benchmark, look to the Dr. Martens 1460 boots as they’ve really nailed the style. 

The Chelsea boots

A Chelsea boot has a cleaner design so they work well for any of your slightly smarter looks or whenever you want to look a little more elevated. There’s a wide range in terms of aesthetic so you’re sure to find ones that are right for you. The ones we have featured here have a slightly heavier sole (similar to the hiking boots), but you can find a plethora of classic soles too that fit this shape of boot.

Toby's top picks

Photographed: Dune London Cloudy Grey (£150)
Photographed: Reiss Amwell Suede Hiking Boots (£238)
Photographed: Grenson MILO (£430)

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Words: Yasmine Kennedy
Styling: Toby Standing