Shorts, T-shirt, trainers – job done. Dressing for summer isn’t exactly rocket science, is it? The cooler half of the year, on the other hand, can present more of a challenge. The colours, the layers, the dizzying selection of outerwear options, the annual struggle of trying in vain to work out if that beanie actually suits you.

Dressing for the cooler months needn’t give you brain freeze, though. The trick lies in having a solid selection of go-to clothing combinations that you know will always work. Failsafe outfits you can throw on without a second thought, and without looking like a man who dressed himself in the dark, no matter how grim the weather.

Maybe it’s a winter date night outfit or armour for kicking up leaves on a stroll in the park. Whatever – here we share a selection of foolproof looks to carry you through the colder months in style.

Check Suit + Mac + Rollneck

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Frosty mornings and icy evenings might spell disaster for your central heating bill, but they’re good news where suiting is concerned.

Cold weather means increased options in terms of experimenting with outerwear, getting creative in the footwear department and even swapping the traditional dress shirt out for something completely different.

Texture and pattern are powerful allies when the mercury begins to drop, too. Just keep it subtle. A low-key checked print can be deployed to add a focal point, while the tactile aspect created by using a knitted rollneck in place of a shirt will lend depth. Colour-wise, stick to neutrals, creating pops of colour with navy or autumnal tones, like maroon and burnt orange, where appropriate.

Bomber Jacket + Jeans + Canvas Trainers

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Don’t let the subzero temperatures outside sabotage your love life. With the right outfit at your disposal, date night can still be on the cards even when the weather is less than tropical.

First port of call in nailing this look is selecting the right outerwear. It should be something that says smart without saying stuffy, too. In our experience, there are few garments better at that than a simple wool bomber jacket. A casual silhouette elevated by a premium fabric, that can easily be dressed up or down depending on the type of date.

Jeans are a safe bet nine out of ten times. The more casual the date, the lighter you can go with the wash. Up top, layer a classic Oxford shirt with a knitted crew-neck and tie the look together with a pair of no-frills canvas trainers.

Technical Parka + Sweatshirt + Cords

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You don’t need to be a fashion insider to know that anything remotely outdoorsy is trending hard right now. Technical outerwear may have been designed with mountain life in mind but now that it has been repurposed for the urban environment it’s plain to see its merits don’t end when you leave the trail.

We’re not suggesting you should start emulating the dress sense of Bill Oddie garment for garment, just that it might be worth considering the odd crossover piece.

Take your coat, for example. A technical parka has long been the go-to for Arctic explorers, polar researchers and anyone else who needs to push their outerwear to the limit. Keep the rest of the outfit grounded with casual staples like a crew-neck sweatshirt and sneakers.

If it needs a dash of texture to spice things up, don’t be afraid to go corduroy in the legwear department.

Plaid Shirt + White Tee + Chinos

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A simple look, but an effective one nonetheless, the plaid shirt/white T-shirt/chinos combination has equal hints of skater, band member and student about it. It’s inherently casual, but can be worn in a variety of ways – go slim black jeans and open shirt for an indie-rock inspired look, or wide-legged pleated trousers and a shirt tuck for something a bit more ‘1950s beat poet’.

The plaid shirt is your weekend wardrobe’s best friend. It’s not too smart, not too sloppy, it’s super versatile, and, perhaps most importantly of all, it’s pretty good at hiding stains should you happen to spill a pint on a Saturday night pub crawl.

Taking the cool weather into account, choose a plaid shirt made from nice thick flannel material and layer it open over a well-fitting plain white T-shirt. Select a pair of contrasting chinos for legwear – if the shirt is light opt for dark chinos and vice versa. To complete, go for either simple suede shoes or a pair of white sneakers for best results.

Chore Jacket + Breton Top + Wide-Leg Trousers

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They called it a trend, yet with every passing season it becomes clearer and clearer that workwear is here to stay. Practical, durable, timeless and rugged, it’s a style you can count on daily, but particularly in the cold weather.

The thing about workwear is the more you layer, the better it looks. A gilet here, a denim jacket there. Perhaps even the odd heavy-gauge roll-neck when the temperature calls for it. For simplicity’s sake, though, we’re going to keep this one easy.

Starting from the bottom up, a pair of canvas sneakers is a good place to start. High tops are the seasonally appropriate option and colour is really a matter of personal preference. We would suggest, however, that if you choose something bright, to ensure it isn’t fighting for attention with any other parts of the outfit.

Further up, wide-leg trousers are a workwear staple and will help to balance out proportions when you start adding layers to your torso. Speaking of which, set the foundation with a Breton top, adding an overshirt, chore coat and perhaps even a parka or canvas gilet if it’s cold enough.

Overcoat + Trainers + Baseball Cap

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Looking put together doesn’t have to mean strutting around everywhere in a tailor-made three-piece suit. In fact, a big part of it is being able to confidently mix smarter looking pieces with casual menswear staples. This merging of dress codes is often referred to as “high/low” dressing and has become an integral part of modern menswear.

To really pull this look off, you first have to understand which pieces should be “high” and which should be “low”. For example, patent-leather Oxford shoes and tracksuit bottoms = no, cropped dress pants and white leather sneakers = yes.

One constant in high/low dressing is the outerwear. A smart overcoat paired with a baseball cap and sneakers is the textbook ‘fit; the outerwear working to elevate the more relaxed pieces, achieving an overall balanced look. Layer with a nice heavy roll-neck that contrasts with the coat and you’re good to go.

Statement Jacket + Rugby Shirt + Jeans & White Trainers

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A statement jacket is a must in every self-respecting man’s wardrobe. Something a little bit different that can be called upon to add a touch of personality to even the most basic of looks. This can take the form of a vibrant block colour, a jazzy pattern or even just a subtle print. Where winter is concerned, however, the obvious choice is a Del Boy-approved shearling coat.

Classic shearling outerwear is a powerful weapon when wielded correctly. Just steer clear of gold sovereign rings and medallions and you should be ok. Aside from that, the secret to pulling off such an attention-commanding garment is in ensuring the rest of the outfit is relatively laid back.

This would be a good place to give the rugby shirt trend a go. The refined preppiness is a nice contrast to the outerwear’s balls-out swagger, and some subtle autumnal tones can lend the combination a hint of ’70s goodness if approached with consideration. Denim-wise, a lighter shade will work well. Somewhere between a mid wash and full-blown stonewash would be light enough to compliment the darker tones in the rugby shirt, yet still dark enough to make a pair of white sneakers pop.