“Now is the winter of our discontent, made glorious summer by a well-chosen wardrobe” – Richard III; Act 1, Scene 1 (Don’t look it up, just trust me on this one.)

The bard’s nailed it yet again, codpieces notwithstanding. Because even though the arrival of winter ushers in a period of shortening days, plummeting temperatures, cracked lips and familial Mexican standoffs, it also presents an opportunity to flex your sartorial muscles.

In these cruel climes (and in Mexican standoffs, come to think of it) we’re told it’s a case of the more cold-deflecting clobber, the merrier. But we’d like to put forth the case that less, in fact, is more. Truth be told, with just a few well-chosen items, your winter wardrobe can be transformed into a revolving carousel of looks and outfits to suit every eventuality under the sun (or the driving sleet, for that matter).

Oxford Shirts

The Oxford shirt is a dear old friend: a man for all seasons that’s there for you in both work and in play; in sweltering heat and murderous cold.

In winter, the evergreen garment likes especially to show off its Ivy League roots: the button-down collar brings a faintly preppy nod to a crew neck sweater, while the shirt’s soft, coarser weave cotton means it can stand up to the declining temperatures when slid underneath a wool overcoat.

As the cold rolls in, stick to classic colourways like white, powder blue and slate grey, or try experimenting with on-trend autumnal hues.

Men's Oxford Shirt Outfit Inspiration Lookbook For Autumn/Winter

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Men's Oxford Shirts

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Neutral-Coloured Long-Sleeved Tees

Menswear writers preach the virtues of ‘layers’ like a slightly desperate onion salesman. But a layered look is only as strong as its weakest link. Set your foundations in stone with a well-chosen long-sleeved tee.

Long-sleeved T-shirts do their best work in a neutral palette (think shades of grey, white and beige), where they can sit as the blank canvas for your more adventurous style exploits. They also lend a robust, casual underpinning to overshirts and Oxfords, and form a welcome last line of defence against winter’s piercing winds.

Men's Long-Sleeved T-Shirts Outfit Inspiration Lookbook For Autumn/Winter

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Men's Long-Sleeved T-Shirts

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A Hoodie

The streetwear staple that broke free of its sporting roots (not to mention the clutches of David Cameron, whose reign it long outlived), the hoodie is a smart-casual stalwart that can be deployed in the winter months to great effect.

A lighter weight style works well when dressed up – underneath a woollen overcoat for a slightly nineties sheen – or dressed down under a leather or denim jacket, teamed with a good-quality cotton tee with tapered sweatpants. Zipped numbers are particularly useful for layering, while the oft overlooked half-zip variant can add a collegiate slouch to an Oxford shirt.

Men's Hoodies Outfit Inspiration Lookbook For Autumn/Winter

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Men's Hoodies


A Plain Sweatshirt

A cornerstone of the male wardrobe, this timeless piece has its roots in workwear and athletic apparel. As such, it’s ideal weekend attire – whether you’re gym-bound or running errands.

Hardwearing and easy to care for, the plain sweatshirt often gets better with a little wear and fade. Opt for a heavyweight number in a neutral colourway this winter.

Men's Plain Neutral Sweatshirts Outfit Inspiration Lookbook For Autumn/Winter

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Men's Plain Neutral Sweatshirts

SUNSPEL Loopback Cotton-Jersey Sweatshirt - Click to buyzara BASIC CLOSED SWEATSHIRT - Click to buyMAISON KITSUNÉ TRICOLOUR FOX CREW SWEAT - Click to buyASPESI Loopback Cotton-Jersey Sweatshirt - Click to buy

An Overshirt

The overshirt, or shacket, is a hybrid piece that sits at the mathematical centre of the winter wardrobe: a crucial mid-layer between lighter shirts and heavier outerwear.

It originated in mountaineering gear and military uniform, and the overshirt’s certainly as versatile as that heritage suggests. Try it in heavy cotton twill or wool for a rugged, natural look; in suede or a quilted fabric for a higher-end feel; or in nylon and synthetics for an athletic lean.

Men's Overshirts and Shackets Outfit Inspiration Lookbook For Autumn/Winter

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Men's Overshirts and Shackets

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A Shearling (Or Faux Shearling) Jacket

It’s not hard to see why the shearling jacket is an undying outerwear favourite. Both masculine and luxurious, practical and decadent, the sheepskin-and-wool rough cut has garnered a cast of apostles that includes James Dean, Biggles, Marlon Brando and Alain Delon (and just about everybody else).

With their rugged air force and motorsports roots, shearling jackets do their best work over heavier cotton, chambray and plaid shirts, or with heavy roll neck jumpers and dark jeans. As is often the case with statement jackets, less is more here: avoid cluttering up the contrast collar with scarves or accessories.

Men's Shearling Jackets Outfit Inspiration Lookbook For Autumn/Winter

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Men's Shearling Jackets

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A Camel Overcoat

Ah, camel: beige’s better-looking big brother. The warm, caramel-tinged hue has long been admired by designers for its versatility and wearability – unlike the more anaemic beige, for example, there’s very few skin and hair tones that camel doesn’t complement – and is experiencing an unmistakable renaissance in the outerwear game.

In its various incarnations, a camel overcoat can either lend a chic, continental feel to an outfit, or take it for a pleasingly retro spin. Drape it over all-black-everything to beat the Parisians at their own game, or dress it down with jeans and a grey marl sweatshirt.

It also makes for a great companion for office wear in almost any form, flexing between smart-casual and formal dress codes with ease.

Men's Camel Overcoats Outfit Inspiration Lookbook For Autumn/Winter

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Men's Camel Overcoats

suitsupply LIGHT BROWN OVERCOAT - Click to buyriver island Tan smart overcoat - Click to buytopman Camel Wool Rich Overcoat - Click to buyACNE STUDIOS Garret Melton Wool Overcoat - Click to buy

Slim Dark Selvedge Jeans

Selvedge jeans, especially the much vaunted Japanese variant, pull even more persuasively at the purse strings come winter.

The traditionally crafted seam (which is notable for its red or orange inside thread) is mostly deployed on thicker, more expensive denim cuts that mould to your body and insulate against the cold far better than any watered down, 1 per cent elastane modern alternatives.

Wear a slim or straight fit pair over Chelsea or chukka boots.

Men's Slim Dark Selvedge Jeans Outfit Inspiration Lookbook For Autumn/Winter

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Men's Slim Dark Selvedge Jeans

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Grey Tapered Sweatpants

“Don’t be the guy at the bodega on Saturday morning in sweatpants and shearling-lined house slippers, ordering an egg sandwich like no one else in the world exists,” said GQ US last summer in a rant against the uglier face of loungewear. And, while the magazine’s correct about the egg sandwich, they’ve overlooked the sheer joys of a decent pair of sweatpants.

The difference between perennial sports science student and man of athleisure is tailoring. A tapered sweatpant lends a more elegant silhouette to the soft lines of the fabric, while a well-fitted pair (nothing too baggy, tight or long in the crotch) will stop you looking like a Jack Wills seasonnaire.

It’s also wise to pick your moments. Air travel? Yes. Night out? No. Day off? Yes. First date (or second, or forty-third)? No.

Men's Grey Tapered Sweatpants Outfit Inspiration Lookbook For Autumn/Winter

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Men's Grey Tapered Sweatpants

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A Wool Suit

Sheep don’t get enough credit: wool is a remarkable material. Warm enough to guard against the belly-flopping temperatures, yet breathable enough to survive a rush-hour commute’s trials of fire, wool suiting is the textile of choice for the modern winter wardrobe.

Its lightly peached texture also safeguards against the dreaded shiny suit syndrome, and its traditional feel is at home in the dark, flattering hues of the season. Plump for a navy or charcoal number to anchor almost any shirt and tie combination.

Men's Wool Suits Outfit Inspiration Lookbook For Autumn/Winter

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Men's Wool Suits

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Leather Sneakers

A decent pair of leather sneakers can handle a staggering array of eventualities. From lazy Sundays to smart-casual gatherings and even a seasonal twist on formal suit separates, an understated, well-made sneaker is the go-to shoe for a space-strapped weekend bag.

More comfortable than a traditional shoe, but smarter than an athletic trainer, leather sneakers are a forgiving option for long days on your feet. Go for a traditional colourway, like the classic tennis white, or a muted tone such as dark grey or beige.

Men's Leather Low Top Sneakers Outfit Inspiration Lookbook For Autumn/Winter

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Men's Leather Low Top Sneakers

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Chelsea Boots

Hardwearing and all-weather (suede excepted), yet still sleek enough to wear with a well-cut suit if you need to, the Chelsea boot is a timeless cornerstone of a man’s cold-weather wardrobe.

It chimes with almost any type of trouser, from denim to chinos to smarter styles. Opt for the best quality you can get your hands on (cheap Chelsea boots are a leaky false economy) and steer well clear of anything Rip Van Winkle-pointy.

Men's Chelsea Boots Outfit Inspiration Lookbook For Autumn/Winter

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Men's Chelsea Boots

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