The best winter hats for modern men in 2022

The importance of a good winter hat cannot be emphasized enough. It is often said that much of a person’s body heat is lost through the head (a myth by the way), but less talked about is the fact that all their reputation on the street can be lost due to bad headgear.

Men love to say that ‘hats just don’t fit me’, but the truth is, those guys haven’t found the right one yet. Yes, these cold weather accessories have the power to make or break winter outfits, but to get it right you just need to have a basic understanding of the different styles available and which of them will work for you as an individual.

Admittedly, this is easier said than done. There are many options available, many of which require a wide berth, so to make things easier for you, we’ve put together this handy guide to all the different winter hats that deserve your attention, along with some styling tips and advice on who will fit them.

the bonnet

What is it?

A beanie is a type of woolen hat that has become the winter headgear for the modern man. It can be with or without cuffs and usually has a ribbed construction for a stretchy, comfortable fit. It was originally designed to keep workers warm outside during the colder months.

Who is it suitable for?

The reason beanies are so popular in menswear today is because they fit almost everyone. It’s a simple style that’s hard to go wrong, provided you don’t pick one that’s way too big for your head. or a color that clashes wildly with your skin tone.

How to style

Again, this is the great thing about a beanie: you can wear it with almost anything. We recommend buying a beanie in a versatile neutral color that can transition smoothly from outfit to outfit. Plain old wool is all well and good, but luxury versions in cashmere, merino and angora are even better in terms of insulation and comfort if you want to spend a little more.

The Trapper Hat

What is it?

Designed for the absolutely harsh winter conditions, the trapper is a heavyweight, padded hat, with large ear flaps that can be clipped to the top when not in use. It was originally created for fighters in the 17th century and is very similar in appearance to the Russian ‘ushanka’ hat and the ear-flap aviator hats worn by early airplane pilots.

Who is it suitable for?

Due to its voluminous shape and large profile, a trapper hat is not the best option for anyone with a small head. It’s also incredibly warm, meaning it’s only really suitable for people who live in places where winter temperatures routinely dip below zero.

How to style

Large, bulky hats work best with large, bulky outerwear. Trappers are designed for the coldest conditions, so it only seems right to pair one with something equally important, like a good down jacket or puffer jacket. Aside from that, stick to casual wear – this is not the kind of hat you would wear to an evening wear dinner and should not be paired with tailoring.

The fisherman’s hat / watch hat

What is it?

First worn by weathered fishermen in Europe, this undersized cuffed beanie has since made its way to cities, and on the heads of heritage-hungry workwear-obsessed hipsters and fashionistas. It is very small, covering only the top of the head and sitting just above or behind the tips of the ears.

Who is it suitable for?

The fisherman’s beanie’s low profile means it doesn’t add height to the top of the head. This makes it a good option for those with long faces who find that a traditional beanie elongates their face in an unwanted way. For men with round, broad faces, the opposite is true.

How to style

Workwear staples like overshirts, denim jackets and raw selvedge denim speak to the blue-collar roots of the fishing beanie and will always work well. Keep your fabrics heavy and textured, and colors muted and earthy.

The heavyweight baseball cap

What is it?

Traditionally, a baseball cap has been a summer hat, but thicker fabrics and added details are often used by brands and designers to make this headwear hero suitable for inclement weather and icy temperatures. It’s still a classic cap with a prominent peak, but with materials like felt, wool and corduroy instead of traditional canvas or twill.

Who is it suitable for?

In terms of face shape, baseball caps suit everyone. However, due to the fact that a baseball cap does not provide any kind of ear coverage, people in locations with extremely cold winters may want to consider something more substantial.

How to style

Wear a winter baseball cap with casual clothes. It works well as part of sporty casual-inspired winter looks, so try pairing it with things like hoodies, joggers, sweatshirts and puffer jackets.

The bulge / ski hat

What is it?

A bobble hat is a woolen hat with a knitted bobble on the crown. The bulge is mostly decorative today, but in the past it was there to hide the finish of the knit and make it look neater. There are those who say that it was also loved by fishermen, as it provided light protection against the top of the head.

Who is it suitable for?

If you have a long face, stay away from bobble hats. The bulge adds height which can make the head look disproportionately long. It’s also not the most serious hat, so if you’re looking for something to keep you warm at a winter funeral, you might want to reconsider.

How to style

The bobble hat has quickly become a streetwear staple, with Hypebeast favorites like The North Face, Noah and Aime Leon Dore all producing the style in its seasonal collections. So try pairing it with hoodies, logo t-shirts and modern prep pieces for instant compliments. Alternatively, if you’re more practical by nature, the bobble hat is always at home with winter-ready down outerwear and a pair of traditional hiking boots for a ski-travel-friendly look.

The earflap cap

What is it?

A fully winter-proof version of a classic baseball cap, this peaked cap features insulating earmuffs that can be worn down or tied when not in use.

Who is it for?

An earflap cap is a good option for anyone living in a sub-zero location who likes the look of a baseball cap but is put off by the lack of headgear.

How to style

Wear an earflap cap with similar outdoor workwear-inspired pieces. Try layering with things like a flannel shirt, jacket and down parka, and tie it all together with some raw denim and leather boots.

The flat cap

What is it?

A round cap with stiff peaks, originating from the British Isles and usually made of wool, tweed or cotton. It is a traditional style that has been around since the 18th century and has close associations with golf and rural activities.

Who is it for?

A flat cap is a great option for lovers of classic style or for those who just want to introduce elements of it into their modern wardrobe. Unfortunately, like a baseball cap, it doesn’t cover the ears, so may not be the best option for very cold locations.

How to style

Be careful not to get too caught up in the old-fashioned aesthetics when styling a flat cap. Remember, this is not a Peaky Blinders cosplay. Forgo tweed cardigans and sport coats in favor of modern-classic pieces. Think button-down shirts, unstructured blazers, turtlenecks, knit polo shirts and jeans.

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