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Style Advice

The hardest-working boots of the season

The hardest-working boots of the season

You probably know as well as we do that boots are the MVP of your winter wardrobe. They can be dressed up or down, they suit just about anyone, and even smarter pairs can be fully functional when you’re facing the elements. Whether you favour sturdy leather lace-ups or a sleek-cut Chelsea style, you can guarantee your cold-weather footwear will be on top of your wardrobe’s rotation throughout the season. 

But it’s not just about style (although we know it helps). You’ll also want to be assured that you’re stepping out in truly strong and sturdy footwear that will withstand the test of time, as well as the wind, rain, and snow. We called on Thread stylist Freddie Kemp to unbox the boots that will carry you through country walks, cold commutes, and countless pub crawls for years to come.

Photographed: GANT St Grip Mid Lace Boots ($142)

Hikings boots

No longer reserved for dads and dog walkers, the hiking boot is now a certified staple shoe. With its rise in mainstream popularity came an increase in more refined and easy-to-wear takes on the technical style, meaning hiking boots are now officially a shoe that can look good with your weekend look, even if you’ve no predilection for a country ramble. 

Even champions of outdoor clothing like Patagonia and Columbia have jumped to it and designed hiking boots for the everyman that are just as comfy and practical but look sleeker and more considered – so you know it’s a trend that’s sticking around.

What to look for

“Contemporary hiking boots still come in sturdy shapes, but don’t feel too chunky around the ankle so are easier to match with the rest of your wardrobe,” says stylist Freddie Kemp. 

When choosing the right hiking boots for day-to-day wear, look for a weatherproof textile like canvas and sturdy rubber sole. Not only will they say comfy and durable for years to come, they’ll also be super easy to wash and keep clean. 

How to wear them

Style-over-function hiking boots will have less padding around the ankle, so work well with the silhouette of rolled-up selvedge denim jeans or wide-leg trousers. “The look has a utilitarian feel that’s timelessly rugged and perfect for winter,” Freddie says. Plus, if the trend doesn’t stick (though we think it will), you’ve got a practical pair of boots for when the mood strikes to take a hike.

Chelsea boots

If you don’t already own a pair of Chelsea boots, this is the year to invest. Although popularity with horse riders has given them countryside connotations, the style was adopted by the 1960s mod scene and has been an urban wardrobe staple ever since. The sleek, single-panel upper of leather Chelsea boots lends a smarter feel that’s perfect for lifting casual outfits into more refined territory, or pairing with tailoring on winter days where your smart shoes may not survive the elements.

Shot at Boys Hall

What to look for

“If you want your Chelsea boots to look smart and considered in any setting, go for a plain black leather pair with a rounded toe,” Freddie says. They feel clean and minimal and can be paired easily with formal trousers, jeans, or chinos. Brown and suede versions, and styles with the elasticated plackets in contrasting colours can resemble a riding boot, which corners them further into country style. 

How to wear them

If you’re leaning into the trend of more interesting silhouettes this winter, these are the best boots for the job. Unless you’re a pin-legged indie frontman, forget the skinny jeans and Chelsea boots look – which is generally much more flattering for feminine figures – and embrace a wider leg. “Not only will be it more flattering to your body shape, it will also make your legs look longer and the shape of your boots will complement the wider hem of your trousers,” Freddie says.

Photographed: Grenson Joseph ($395)

Leather lace-up boots

Every year, the lace-up leather boot makes the cut. “They work for smart events, days outdoors, and everything in between which is a testament to their timelessness, and could earn them the title of ‘Hardest-Working Boots’,” Freddie says. The sturdy leather lace-up is classically stylish, gives your feet and ankle full coverage against the elements, and if you invest in a good quality leather, they’ll only get better with age.

What to look for

A leather boot with Goodyear welted soles will ensure that even your best-loved pair will last for years to come. “They mould to your feet and are easy to re-sole, so are worth the financial investment,” Freddie says.

Although almost any lace-up boot will provide the timeless winter look you’re after, the plainer aesthetic, the easier they are to pull off with anything. Avoid brogue styles that feel naturally smarter and less suited to outdoor wear. A plain pebble-grain leather will keep your boots interesting and still versatile enough to wear with both smart and casual outfits.

How to wear them

The beauty of leather boots is that you can wear them with just about anything (have we said that enough?). Pair with selvedge jeans and a wool coat, a tailored suit, or a relaxed polo and chinos, and they’ll work just as well every time. For true timelessness, a brown is the most versatile colour, while black leans smarter and tan fits best in rugged workwear looks.


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Words: Ella White
Photography: Jack Batchelor
Styling: Freddie Kemp