Get stylish up top - 5 best winter hats for men

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Hats in general can be hard to pull off. Whether you’re looking for pure warmth or a bit more attitude, when the temperatures drop, make sure you have something stylish up top. From classic to more vibrant designs, no matter what your look and budget, here are some of the best on offer for autumn/winter 2017.

Hats exclusively illustrated by Joseph Larkowsky (@josayhef)



Beanies bypass all rules of hat-wearing. The knit style has a simple, universal quality that makes it look just right on anyone. Plus, it keeps your head warm, disguises bad hair days, and adds an easy detail to every outfit. Our pick is from Drake’s, the British menswear haberdasher, founded in 1977 and built around Mr Michael Drake's philosophy of 'relaxed elegance.' Their blue Donegal Merino Wool version is spun with vibrant orange, red and green merino yarns.

Available at £55



While most of us can carry off a hat of some kind, not everyone can pull off a trilby. If you can, good for you and we recommend you go for a bold colour to bring a bit of stylish drama to winter days. The trilby hat’s name, sometimes also known as the ‘brown hat’ in Britain, comes from a play. During the stage adaptation of George du Maurier’s 1894 novel Trilby, performed in London, a hat of this style was worn and so the trendy trilby hat was born. Our favourite is Paul Smith’s cobalt blue trilby with a black grosgrain headband complete with feather.

Available at £135


Bobble hat

The humble knitted bobble hat is very much in vogue and the joy of a great bobble hat is in its simplicity. It’s warm, cosy and easy to throw on with any outfit, and the more colourful the better. We couldn’t help but go for Burberry’s cashmere-wool beanie in a bright Fair Isle pattern. The design fits snugly with a turnback hem, and is topped with a playful pom-pom.

Available from £150


Flat cap

Yes, the flat cap can have a little Oliver Twist energy to it, but when braving the winter temperatures with your collar turned up, it's really "dapper British gentleman" that comes out most and who wouldn’t want that compliment? The main thing to remember when styling a flat cap is that they’re not like beanies. When you wear a flat cap it takes centre stage, and the rest of your outfit needs to be built up around it. We love the effortless style of Barbour’s Moons tweed cap from the renowned British mill, Abraham Moon & Sons.

Available from £37.95



If the weather starts hitting arctic temperatures, the biggest drawback of the other styles is their incomplete coverage: the lower part of the ears is left bare, as are the cheeks and chin. Looking to stay extra warm this season? Go for the (faux) fur-trimmed trapper, or ushanka, achapka or “Elmer Fudd” (after the iconic Loony Tunes character), which solves the problem by adding two flexible flaps, one on each side. Our cosiest choice is the navy ‘BEARDY’ from Ted Baker with its soft faux fur lining and branded detailing.

Available at £45

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