They say that you can tell a lot about a man by the shoes he’s wearing. Which is entirely true, except that, during the colder months, your feet are not necessarily the first place people will be looking. The claim – first put about by the US military – that you can lose something like 40 to 45 per cent of your body heat through your head has been long since debunked by medical science, but that doesn’t mean we’re planning on spending winter with a chilled noggin. And so, a warm hat becomes a necessity at this time of year – but, in terms of what you wear, also something of a focal point. Your headgear, then, cannot be an afterthought, but when your brain is frozen, which to pick becomes even harder to think about. Thankfully, Mr Stephen Doig is here to ensure that this year, no one pulls the wool over your eyes.

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Woolly hats – what style and colour to go for, and how to wear one?

From @bendatmo via Instagram

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The gap between the sartorial ideal and the harsh reality is never more keenly felt for a man than in the hat department. You aim for Mr Robert Redford as Jay Gatsby in a pristine Montecristi Panama hat, you end up looking like you’re auditioning for an amateur production of Guys And Dolls. Winter hats are of course a different beast and one we’re eyeing up now that the temperature has plummeted, but for every Mr David Beckham in a beanie hat there’s a Compo from Last Of The Summer Wine, a character in the 1980s British sitcom known for his shabby appearance and moth hole-ridden wool hat.

One pertinent point to bear in mind from the get-go: unlike other hats such as the fedora or Panama that are more gently “placed” on the head, woollen winter hats will ruffle your hair up. Fine (in fact, even more necessary) if you’re lacking up top, but requiring a degree of thought and planning if your end destination through the arctic blasts and lashing winds is the formal environs of an office. If your commute to work is particularly bracing, there are smarter variants on the woolly hat that can work more harmoniously with a smart suit and coat than others.

For example, smaller, neater interpretations, such as this one, are less shaggy and outdoorsy, and the neutral colour works easily into a more corporate uniform. Just make sure you have some hair wax at your desk. From there, we move into more heavyweight, outdoors-appropriate versions. Generally, while fashion clamours to claim the beanie hat amid a fit of 1990s revival themes, it’s wise to stick to the cleaner, more minimalist varieties. A version in solid wool, perhaps with cosy ribbing or a cable-knit motif will happily complement a rugged jacket and a rosy-cheeked winter walk. Moss and natural tones such as this, as well as greys and monochromes, will generally work fluidly with most wardrobe items.

From there, we veer into jauntier and more obviously festive territory. This is no bad thing, and in fact can feel right at home on ski breaks or festive vacations; if you’re staying in snow-covered New England, you might as well go full Christmas with Norman Rockwell in a bauble-bright red number with a merry little pom-pom. At the opposite end of this cosy, twee vignette are the more urban takes on woolen beanie hats, as seen in the gritty stylings of Off-White and Balenciaga. Great if you’re part of that Supreme-laden contingent, but a tad try hard if street style isn’t your natural habitat. And if your winter is more Greenwich Village than alpine village and you’re of a more cutting-edge sensibility, by all means opt for a more all-out fashion approach. Acne Studios’ zinging neons will look suitably impactful with a puffer (and stand out like a beacon in a whiteout), and Loewe’s aping of normcore geography teacher outerwear will earn you style kudos even as the temperatures plummet.