On a scale of one to unspeakably awful, waking up in the morning in winter ranks bitterly close to the latter. Unsheathing from a duvet’s warm embrace is basically a reckless act of self-sabotage and you can forget about your eyelids staying open for consecutive seconds too, that’s never going to happen. Faced with this debilitating set of conditions the task of putting clothes on – let alone choosing them wisely – is fiendishly difficult.

To avoid just going out in a sleeping bag, what every man needs at this time of year are easy-to-digest, unthinking ways to stay warm and look good. So let’s keep it simple. Smart or casual, these are our failsafe winter outfits that that won’t leave your style out in the cold.

Shearling Jacket + Roll Neck + Wool Trousers

While we’re passionate advocates of looking your best whatever the season, your mum is correct: practicality is paramount come winter. Practical doesn’t mean devoid of visual appeal though. Take the shearling jacket, for example. Not only does it look like a dreamily wearable shagpile, it comes highly recommended by mother nature herself. Plus, as we’d expect from an item of clothing that’ll leave you light of wallet, a classic tan shearling jacket has shedloads of charisma (and years of wear) so you get the right kind of attention without putting in too much graft with the rest of your outfit.

To ramp up the style’s natural appeal, err closer to Steve McQueen than Del Boy. The trick lies in avoiding anything too casual. Team your shearling with a roll neck rather than a crew or V-neck knit: grey, black, navy or even burgundy all work well with a tan shade. For your bottom half, avoid the instinct to reach for a pair of jeans as this will bring out your shearling’s inner scruff. Dark wool trousers (bonus points for pleats) and Derby shoes will add some welcome formality and are handy for keeping your legs and feet frostbite free.

Shearling Jacket + Roll Neck + Wool Trousers Products

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Denim Jacket + Overcoat + Beanie

If you’re one of those annoyingly organised types who actually packs away parts of their wardrobe season on season, halt before you banish your denim jacket until spring: it’s the winter layering piece that you never knew you needed. From a purely superficial point of view, blue denim does a heroic job of sprucing up whatever it’s sat next to while simultaneously bolstering your defence against the elements.

Your layering options are pretty comprehensive too here: a coat in brown, grey, navy, black, camo or green will all reap the benefits of cosying up to a denim jacket. Our top tip though is a move favoured by menswear deity Johannes Huebl, which requires you to whack a herringbone grey overcoat on top of your denim jacket.

Thanks to this combo’s high/low fence-sitting nature, the rest of your outfit can happily pilfer pieces from both your smart and your casual wardrobe. So, add a beanie hat into the mix (we favour short, ribbed fisherman styles over those that reach unappealing down the neck) to add casual contrast to your overcoat’s formality. Who said being indecisive was a bad thing, eh?

Denim Jacket + Overcoat + Beanie Products

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Bomber Jacket + Jeans + Chelsea Boots

Unless you’re a bouncer, part of a questionable subculture or both, a bomber jacket isn’t necessarily part of your permanent winter outerwear line-up. This is an oversight though because it’s invaluable for its ease of wear and impeccable insulating credentials. And in teal, cobalt blue or burgundy, it neatly sidesteps any association with those pesky clipboard-wiedling hardmen too.

Choosing cold weather companions for your bomber jacket is thankfully a pretty laid-back affair. Any of the wardrobe basics that you take for granted are probably appropriate: the simple combination of grey crew-neck jumper and blue slim-leg jeans, for example, is ideal. The only thing you’ll have to pay extra attention to is your footwear. Unless you’re some swaggier-than-thou streetwear kid with legions of likes and surging hormones, avoid trainers. Choose some Chelsea boots instead, crafted from suede and taken in either brown or tan to avoid encroaching skinhead vibes.

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Flannel Shirt + Wool Trousers + Hiking Boots

There are few things from a rambler’s repertoire that we’d recommend repurposing for yourself, but we’ll make an exception for hiking boots. For anyone who has fallen victim to wet-sock-in-shoe syndrome, the hiking boot is a no brainer: it actually lives up to its promise of actually being practical, not just looking practical.

Working from the ground up, once your feet are clad in these winter wonders you’ll have to make sure that the rest of your outfit avoids classic woodsman vibes. Dark wool trousers will make a far smarter companion than jeans and offer greater insulating properties to boot. Adding a flannel checked shirt to the mix complements the outdoorsy charm of hiking boots, but you’ll need to tread carefully.

A shirt with a blue, black or green base is preferable to red, which is a little too pastiche for our liking. Now all that’s left to do is throw a technical padded jacket on (no denim please) and you’re a walking weatherproof style god.

Flannel Shirt + Wool Trousers + Hiking Boots Products

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Suit + Gilet + Overcoat

For many men, winter style still requires a suit (those smug creative types who can rock up to work in a hoodie can look away now). Despair not, because rather than being a precursor to pneumonia, wearing a suit in winter is an opportunity to master clever layering with the help of the criminally overlooked gilet. Although it may sound counterintuitive to pair a farmer’s favourite layer with the clean lines of a suit, against all odds, it works.

The key to getting a gilet involved in your workwear combos is ensuring that the balance of colours you’re using is on point. A grey or navy work suit will benefit from a tonal take on the gilet, which essentially serves as an extension of your suit.

Contrast works too though: a navy gilet can comfortably be worn over a grey suit and vice versa. To further menswear-ify your winter work look, add a grey check overcoat and you’re basically the best-dressed guy on your commute, even if your eyes aren’t fully open to the competition.

Suit + Gilet + Overcoat Products

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Wax Jacket + Hoodie + Statement Trainers

Heritage menswear has been in retreat for the past half decade, which means that if you revisit this classic genre, you’ll technically be an early adopter and won’t run the risk of wearing the same garms as everyone else. Unsurprisingly, outerwear inspired by outdoor pursuits will actually perform in terrible weather, and a stable of sombre colours (green, khaki, navy, brown) will easily get along with the rest of your wardrobe.

Safe doesn’t mean boring though. Thanks to the heritage jacket’s traditional leanings, anything that feels vaguely modern will provide some contrast and stop you from looking like an actual gamekeeper. So, team with a grey marl hoodie, charcoal slim jeans and bold statement trainers to hit that sweet spot between streetwear and serious adult this winter. It’s basically your way of wearing your comfiest clothes possible while tricking onlookers into thinking you’re not.

Wax Jacket + Hoodie + Statement Trainers Products

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