Every Winter Hat Style To Have In Your Wardrobe This Season

Updated June 1, 20225 Mins read91

In the age of streetwear, we’re an incredibly long way away from the days when a hat wasn’t just something to obscure a bad hair day, but a social necessity. Nonetheless, just because you don’t have to wear one, doesn’t mean that you shouldn’t.

While it may not be factually true that you lose most of your body heat through your head, we can confidently confirm that in most cases a hat will keep snow, wind and rain from tormenting your bonce and ruining your barnet.

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So, with that in mind, here are the only styles worth covering your crown with this season and some indispensable tips on how to pull them off (or on, rather).

The Beanie Hat

Like much else in the menswear canon, the beanie has a chequered history. Designed as a means to keep blue-collar workers’ hair from their faces while grafting, this brimless hat is thought to have been bestowed with its name thanks to the small cloth-covered ‘bean’ at the crown.

Fast forward to the mid-2000s and the style was more readily associated with students sporting a sagging, diaper-esque mass of fabric that tickled the wearer’s neck.

To do the hat justice, make like those savvy Scandi fishermen and choose a short, neat, woollen skull cap that follows the form of your head. These work best worn off-duty at the weekends, particularly when paired with other worker-inspired staples such as an overshirt or denim jacket.

Tesco F&F

The Flat CapIf you take only one sartorial cue from your grandad, make it the flat cap. Most often crafted from insulating wool or tweed, the hat is characterised by its flat rounded shape and small hard front-facing peak.“The traditional flat cap dates back to as early as 1571, when a law was passed dictating that it had to be worn on a Sunday to help bolster the wool trade,” explains menswear stylist Paul Higgins, whose CV includes brands like Diesel, Reiss and Aquascutum. “The hat is now enjoying a renaissance following the success of BBC’s Peaky Blinders, with fans wearing their tweed styles with casual daywear to channel the suave Thomas Shelby.”

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Nailing wearing the flat cap without looking like a farmhand requires bringing it up to date with the rest of your outfit. “There are great high street options out there, but you should invest in a traditional design,” adds Higgins, who suggests wearing one with modern staples like a single-breasted overcoat, a roll neck, and jeans.

House Of Fraser

The Baseball CapNot all baseball caps are created equal. Yes, the style has been hungrily hoovered up by angry adolescents skulking around bus stops, but there are elevated examples of this sports-inspired cranium cover to be had.

“Instead of just wearing a regular cotton cap, update it to wool for winter,” says Sarah Gilfillan, a personal stylist at Sartoria Lab. “Choose plain dark navy or a grey Prince of Wales check to go with more formal outfits and tweed or a buffalo check for casual.”

Irrespective of age, the baseball cap invariably benefits from simplicity. So, opt for a restrained colour palette and avoid logos to keep the style firmly away from pesky pubescent rabble-rousers. Swerve sportswear, too. A choice piece of knitwear will make a much more handsome companion for a premium baseball cap than a heavy duty tracksuit.

Whistles

The Fedora HatUnlike the trilby (which was last seen surgically attached to Ne-Yo’s head), the hat’s pinched crowned, wide-brimmed cousin, the fedora, is far less susceptible to the whims of fashion and can easily be worn in summer and winter.“The fedora is a traditional staple which has gone from the heads of Englishmen on Savile Row to guys across the globe, such is its versatility,” says Higgins. “In winter you should try wearing yours with a blue workwear jacket, a grey marl sweatshirt, loose green military trousers, and some worker boots for a perfect weekend casual look.”The charm of the fedora doesn’t stop there, though. With enough confidence, the hat can easily be worn with everything from a suit to a leather biker. This is one winter warmer that will give you plenty of mileage.

Brixton At Asos

The Baker Boy HatThe baker boy may be old hat amongst old hats, but it’s enjoying a return to form thanks to its status as a regular head coverer of the two great Davids: Beckham and Gandy.For those unfamiliar, it’s a flat cap on steroids: that’s to say it shares the same Dickensian vibes (often made from tweed, boucle and herringbone weaves), but it’s constructed from more panels and has a more voluminous silhouette.

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The baker boy is undoubtedly a statement hat, so the rest of your outfit needs to be clean simple. In practice, that means dark selvedge jeans, polished Chelsea boots, slim-cut overcoats and crew neck sweatshirts. Pastiche is to be avoided at all costs too, so swerve anything which also emits old-school British charm too strongly. So nop tweed or pinstripe suits, please.

M&S

The Trapper HatThough the number of times you might find it appropriate to wear a trapper decreases proportionally as your age increases, we reckon three-year-olds have the right idea. After all, you’re never too old to block cold winds from entering your ears.Trapper hats are undeniably practical, so your eardrums will thank you for learning how to rock one properly. “If you have a narrow face shape, choose one with the extra set of small ear flaps, which will add some width to your face,” says Gilfillan. “For a wider face choose a sleeker fur so as not to add more width.”

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Hirsute men be warned, there are worse perils than looking like a literal lumberjack ahead. “If your hair is long or you have a beard, ensure that you choose a contrasting colour fur to your hair colour, so it’s doesn’t all blend together in a shaggy fuzz,” advises Gilfillan.

Canada Goose

The Homburg HatYou may not be familiar with the Homburg hat by name, but we’re willing to bet you’ve seen it, most famously perched on the head of none other than Winston Churchill. It’s a semi-formal felt style with a single dent running down the crown and has an upturned brim – so on a technicality, it’s miles away from the fedora and trilby, really. In