The Best Winter Hats For Men (And What To Wear Them With)

The importance of a good winter hat cannot be overstated. It’s often said that much of a person’s body heat is lost through the head (a myth, by the way), but what’s less talked about is the fact that all of their street cred can be lost through poor headwear choices.

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

Granted, this is easier said than done. There are a lot of options available, many of which should be given a wide berth, so, to make things easier, we’ve compiled this handy guide to all the different winter hat styles worthy of your consideration, along with some styling tips and advice on who they’ll suit.

The Beanie

What Is It?




A beanie is a type of woolly hat that has become the go-to winter headwear for the modern man. It can be either cuffed or uncuffed and tends to have a ribbed construction for a stretchy, comfortable fit. It was originally designed to keep blue-collar workers warm outside during the colder months.

Who Does It Suit?

The reason beanies have become so prolific in menswear today is because they suit almost everyone. It’s a simple style that’s difficult to get wrong, provided you don’t pick one that’s far too big for your head. or a colour that clashes wildly with your skin tone.

How To Style


Again, this is what’s so great about a beanie – you can wear it with almost anything. We’d suggest buying a beanie in a versatile, neutral colour that can transition from outfit to outfit smoothly. 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’re looking to spend a bit more.

The Trapper Hat

What Is It?




Designed for the absolute harshest of winter conditions, the trapper is a heavyweight, lined hat, featuring large ear flaps that can be tied up on top when not in use. It was originally created for hunters in the 1600s and is very similar in appearance to the Russian ‘ushanka’ hat and the ear-flapped aviator hats worn by early airplane pilots.

Who Does It Suit?

Due to its bulky shape and large profile, a trapper hat is not the best option for anyone with a small head. It’s incredibly warm too, which means it’s only really suitable for those who live in places where winter temperatures routinely drop below zero.

How To Style


Big, bulky hats work best with big, bulky outerwear. Trappers are designed for the coldest of conditions so it only seems right to pair one with something equally substantial, like a proper down coat or puffer jacket. Aside from that, stick to casualwear – this isn’t the sort of hat you’d wear on your way to a black-tie dinner and shouldn’t mingle with tailoring.

The Fisherman Beanie / Watch Cap

What Is It?




This undersized, cuffed beanie was first worn by weatherbeaten fishermen in Europe but has since found its way into towns and cities, and onto the heads of heritage-hungry, workwear-obsessed hipsters and fashionistos. It’s very small, covering only the top portion of the head and sitting just above or behind the tops of the ears.

Who Does It Suit?

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

How To Style


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

The Heavyweight Baseball Cap

What Is It?




Traditionally speaking, a baseball cap is a summer hat, but thicker fabrics and added details are often deployed by brands and designers to make this headwear hero suitable for inclement weather and frosty temperatures. It’s still a classic cap with a prominent peak, but using materials like felt, wool and corduroy in place of traditional canvas or twill.

Who Does It Suit?

In terms of face shape, baseball caps suit everyone. However, because of the fact that a baseball cap doesn’t provide any sort of ear coverage, those in locations with extremely cold winters may want to consider something more substantial.

How To Style


Wear a winter baseball cap with casual clothing. It works well as part of athleisure-inspired winter looks, so try teaming it with things like hoodies, sweatpants, sweatshirts and puffer jackets.

The Bobble / Ski Hat

What Is It?




A bobble hat is a woollen beanie featuring a knitted bobble at the crown of the head. The bobble is largely decorative these days, but in the past it was there to disguise the finishing gather of the knit and make it look neater. There are those who say it was also favoured by fishermen as it provided some light impact protection to the top of the head.

Who Does It Suit?

If you have a long face, steer clear of bobble hats. The bobble adds height which can make the head look disproportionately tall. It’s not the most serious of hats either, so if you’re looking for something to keep you warm at a winter funeral you may want to reconsider.

How To Style


The bobble hat has quickly become a streetwear staple, with Hypebeast favourites like The North Face, Noah and Aime Leon Dore all producing the style in its seasonal collections. Therefore, try combining it with hoodies, logo tees and modern prep pieces for instant kudos. Alternatively, if you’re more practical in nature, the bobble hat is always at home with winter-ready down outerwear and a pair of traditional hiking boots for a ski trip-friendly look.

The Earflap Cap

What Is It?




A fully winterised version of a classic baseball cap, this peaked hat has the addition of insulating ear covers which can be worn down, or tied up when not in use.

Who Does It Suit

An earflap cap is a good option for anyone living in a location with subzero winters, who likes the look of a baseball cap but is put off by the lack of head coverage on offer.

How To Style


Wear an earflap cap with similarly outdoorsy, workwear-inspired pieces. Try layering up with things like a flannel shirt, chore jacket and down parka, tying it all together with some raw denim and leather boots.

The Flat Cap

What Is It?




A round, stiff-peaked cap, originating from the British Isles, and most commonly made from wool, tweed or cotton. It’s a traditional style that has been around since the 1700s and has close associations with golf and country pursuits.

Who Does It Suit

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

How To Style


Be careful not to get too carried away with the old-timey aesthetic when styling a flat cap. Remember, this isn’t Peaky Blinders cosplay. Forgo tweed waistcoats and sport coats in favour of modern-classic pieces. Think button-up shirts, unstructured blazers, roll necks, knitted polo shirts and jeans.

The post The Best Winter Hats For Men (And What To Wear Them With) appeared first on Ape to Gentleman.


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