It’s that time of year when it’s wise to remember these words of wisdom from author and serious all-weather walker, Alfred Wainwight MBE: “There’s no such thing as bad weather, only unsuitable clothing.” With this in mind, alongside a decent winter coat, the most important adaptation for inclement climes is, without doubt, footwear.

A solid pair of boots is your foundation for (virtually) everything life throws at you, and there’s perhaps no greater marriage in the fashion world than your best boots and favourite jeans. Together, they’re two items that look better the more worn in they become – over time their natural materials will take on a look unique to you, and the combination of the two will give you style options all winter.

There’s also a pair of boots for every style preference, from smarter, ideal-for-the-office Chelsea boots, to substantial, all-weather Derbys designed to survive a rained-soaked commute. Or look to the rise in streetwear-inspired silhouettes recently – hybrid trainer-meets-lightweight-hiking-boots for those after a contemporary look.

The choice is endless, and the focus is two-fold; form and function. Get both with one of the following styles, and pairing them with a selection of denim will be a doddle.

How To Wear Boots With Jeans

Chelsea Boots

Brunello Cucinelli

One of the smartest boots of all, the slim round-toe and elegant cut of this London classic was originally designed in the late 1800s for Queen Victoria, no less. Her bootmaker added the functional elasticated sides to the boot, with a pull-on tab at the back, designed to make them easy to slip on or off. Today Chelsea boots have barely changed; two plain pieces of leather form the upper for a clean minimalist look, and combined with its low heel you have one of the most iconic, adaptable styles of boot.

The Chelsea boot still works best in dark colours, as recommended by Tony Gaziano of British shoemaker Gaziano & Girling, who notes that “an elegant pair of boots are these days more important than shoes” and that “a simple black Chelsea is a perfect alternative [to shoes], as it sits neatly under a trouser or jean cuff.” With its more formal roots, we recommend going for black leather, but suede and chestnut brown are also great alternatives that won’t date.

As they’re traditionally a narrower boot with a slightly longer toe, Chelsea boots are ideal with slim-cut jeans in black, grey or navy. They double as perfect office attire, working well with the elevated look of a jacket, shirt and tie while also going smart casual as a weekend city boot to lift more casual jeans. Work the leather regularly with polish or treat them with a suede-protector spray before wearing and you’ll have these boots for a lifetime.

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Desert Boots


Another supremely cool and practical style that has remained unchanged since its inception is the desert boot. Steve McQueen riding one-handed on a Triumph motorcycle in some, with only a pair of raw denim jeans, white T-shirt and white socks is testament to just how good they can look.

Like all great designs, this boot was born out of functionality. During the Second World War, soldiers fighting in the western desert campaigns sought out an alternative to their heavier military-issue offerings, which were impractical on sandy terrains.

The desert boot was the answer. It was made from two pieces of light, supple suede and featured just two eyelets – much fewer than most other boots of the time – which when tightly laced were designed to keep the sand out. And of course there were its flexible crepe soles, which gave better grip and movement on the go.

Today, a desert boot in a light sand-brown suede with its contrast crepe sole looks best worn with the nonchalance of a vintage casual look; think dark selvedge denim jeans, a cable-knit jumper and a casual Harrington jacket or light raincoat thrown over the top. Oh, and if you have a Triumph bike, even better. Embrace the suppleness of the suede and the relaxed look of these boots as they mould to your feet and soften completely.

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Chukka Boots


The desert boot’s smarter cousin, the chukka boot is perhaps the perfect all-rounder. In dark brown suede or leather, it’s a little dressier than the desert style, but it’s an absolute wardrobe staple.

Neutrality and versatility is the key to this boot style. In chestnut suede, they smarten up dark jeans with more casual shirt and blazer or a lightweight jumper and coat. Then, at the weekend for a chilly walk to the pub, wear them with a light-wash pair of jeans, a relaxed bomber jacket or rain mac and a classic plain tee – you could always add in a check scarf to keep things interesting.

If you tend to opt for black jeans, then a black suede version is well worth the effort, especially as an evening style and they always look more considered than basic black leather shoes.

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Work Boots

River Island

As the temperatures really drop and you plan long walks in the park, or a day watching the football or rugby, you’ll soon realise that as cool as your trainers look, after a couple of hours standing in one spot on freezing concrete, they just aren’t going cut it. What you need is a pair of heavy-duty, thick-soled work boots – without any compromise on comfort.

Classic work-wear bootmakers Red Wing nailed the design, comfort, durability conundrum some time ago. Originally designed as industrial work boots, the functionality element is felt in every stitch of their construction, in the tough waterproof leather and the flat-supportive soles. The softer tan leather boots with light rubber soles and mountaineering style laces would look great with heavy selvedge denim, an overshirt and a shearling-lined jacket. For a more dressed up look they’re great with slimmer jeans, a Oxford shirt and a mid-length camel wool coat.

For black denim, celebrity stylist, Christopher Brown recommends, “a black Derby boot worn with biker-style black jeans, a leather jacket or a long black wool top coat and baker boy tweed cap”.

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Hiking Boots


Since time immemorial man has braved the elements and scaled the highest mountains. That performance-driven style has filtered into everyday clothing is testament to the fact that quality has permeated every corner of menswear, and we’ve seen hiking boots take hold of men’s winter wardrobes across the board.

One of the early adopters was Berluti which introduced a luxury version perhaps more suited to the Champs Elysée than the north face of K2. But for the metropolis, a lightweight hiking style is your best option. Military boot makers, Danner offer up one of the season’s best sports hiking boots in a multitude of colours all with lightweight rubber soles. Comfort is paramount here, but paired with the functional elements of the outdoors, they’re ideal to wear with mid-wash jeans, and a complementary puffer or parka jacket. And of course don’t forget the requisite wool beanie à la Edmund Hillary and co.

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Smart Boots

Massimo Dutti

They say you can’t wear brown in town, but we all know such stifling rules are disappearing into the style abyss, and fortunately so. A smart brogue boot with all the elegant stitched detailing can really add something to a traditional flannel suit, or a smart blazer worn with dark denim jeans.

You should follow a couple of simple rules though, as George Glasgow, CEO of British shoemakers, George Cleverley decrees: “Smart winter boots can be both elegant and stylish but also durable. Ideally a solid winter boot should have a Dainite rubber sole for the pavement and the upper should be a grained calf or deerskin.”

This elegant style has a similar shape to a workwear boot but is generally much sleeker, built on sharper lasts with less rounded toes – the key difference between the Oxford and the Derby being the closed lacing system. A dark tan or full chestnut brown brogue boot is a more traditional look than say a plain Derby, and so offers a more mature, classic style, perfect for a Sunday gastro-pub lunch.

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