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5 best hats for winter

Christina Ablahad

Posted by Christina A.

11.29.21

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5 best hats for winter

As winter descends upon us and the days get darker and colder, we all have to think about clothing yet again. When temperatures drop, it’s important to have good headwear that can keep you warm. Naturally, you want something that looks good while it works hard for you.

There are a number of viable options for winter hats, and each provides you with an opportunity to really customize and hone your style. So, we’re going to take you through the five most important styles of winter hats. From fedoras to baseball caps, and everything in between, this is the starter guide to winter headwear.

The rancher fedora

This is a sometimes underrated hat style for a few reasons. First, just about everyone can pull it off. You don’t need a special body type or face type. The rancher fedora is universal. 

That doesn’t mean it goes with every outfit. You have to steer into the rugged look. When you do, the rancher fedora completes the look and provides style paired with functionality. 

If you want to spend time outdoors that isn’t on the slopes this winter, this hat is for you. Tame the wilderness. Go on adventures. Teach an archeology class. Look great the whole time.

man in rancher fedora

A good beanie

Beanies are a winter classic, and they are never going away. They are warm, they look good on basically everyone with a pulse, provide function, and feel like a hug on your head. There’s a beanie for every occasion. You can get an over-the-top beanie with loud colors and ridiculous designs for a snowboarding weekend bender. Or you can get an understated, well-fitting beanie that is perfect for a walk downtown or an evening in the pub. There’s really no limit, and you can create a collection of beanies for every occasion.

If you’re not sure where to start, a Carhartt beanie is a great option. They’re ubiquitous for a reason: They last a long time and look stylish without trying too hard.

man in beanie

The trapper hat

With trapper hats, we are stepping out of the realm of universal style. They look great when leveraged correctly. They can also make you look like a total doofus, so tread lightly.

Here’s the key to a good trapper hat. Think about the function. When you need to stay warm badly enough that fashion can be damned, then trapper hats are among the warmest you will find. If you start from that mentality, then think about what else would go in an outfit that prioritizes warmth and functionality. You can craft that idea into a rugged but attractive outfit.

You can also take a 180 on this. Instead of going for the Fargo look, embrace your inner Russian oligarch. You can match a high-class trapper hat with a great suit and winter overcoat.

man in trapper hat

The newsboy

This is another hat style that doesn’t always work, but when it does, it’s awesome. For those who don’t have a clear image, think of old British news boys and the flat, billed hats they wore. The modern take on that style is still called a newsboy.

These hats are solid, making them relatively warm. They also ooze style. You’ll want to think about early 20th century looks to get the tones right when you work the newsboy. If you put in the proper thinking and effort, you can have a great winter outfit that’s both comfortable and chic.

man in newsboy hat

Baseball caps

Baseball caps aren’t just summer wear. When the season turns cooler, you can trade in trucker hats for heavier baseball caps made of winter fabrics like tweed or wool. As long as the weather isn’t brutally cold, a baseball cap looks great with light winter wear.

Technically, this look really shines in a New England autumn, but when mild weather shows up during your winter, the look still works well.

Also, as guys, we all love our baseball caps and any excuse to wear them. Keep your favorite cap at the ready. It still works for any informal setting throughout the winter, and a good baseball cap is warmer than it might seem.

So here you go. These are the five primary hats of winter. Each has a purpose, and all of them can look amazing on most guys. It’s all about pairing the hat with the right outfit and occasion. If you like to be outside in the winter, do it in one of these top picks. If you need to get formal, remember the golden rule for hats. The higher the top, the more formal the hat.

man in baseball cap

11.29.21

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