How to Wear a Beanie for Men: The Ultimate Guide


This article talks about the ubiquitous beanie and how to wear it in various styles that will complement your face and personality. 

But before we dive in, we have something important that we need to ask you!

Do you remember those days when no one cared about fashion or being stylish and just went to their run-of-the-mill 9 to 5 jobs without thinking about the latest trends? 

Jokes aside, fashion and the continuously emerging latest trends can become slightly overwhelming to interpret. 

And while the milliner will never be out of work, what with hats, caps, and the unobtrusive beanie being a fashion staple, it can be challenging to stand out from the crowd and have a unique style. 

A beanie might look like a super simple accessory, but there is no denying the fact that it adds a special touch to your outfit if worn right. 

Hats are not very difficult to wear, but knowing how to wear a beanie correctly, well, that’s another ball game altogether! 

Before we tell you all about how to style your beanie to suit you we’re going to address the elephant in the room and tell you how exactly how this soft hat came to be known as a beanie.

Origin of the Word Beanie

According to the dictionary, the term ‘beanie’ refers to a small close-fitting hat worn on the back of the head. Ugghh, talk about a “meh!” description. 

But here’s an interesting origin story!

Opinions as to the origin of the beanie differ, but the most popular one is that the word ‘bean’ was slang for ‘head’ decades ago. And hence, something you pulled over your ‘bean’ came to be called a beanie.

Fun fact: The baseball cap was inspired by the concept of a beanie with a brim!

Why Should You Get Yourself A Beanie? 

Asking yourself if you should give in to all those Pinterest and Instagram looks and finally get yourself a beanie? 

To be honest, a beanie is so much more than just fashion and looking your best. 

Here’s why you should get yourself one!

An Evergreen Fashion Statement

Wearing the beanie was always popular among college freshmen. 

Any winter university campus over the world is a veritable ocean of beanies. And yet in today’s “do it for the gram world,” wearing the beanie is one of the easiest and trendiest ways to add a contemporary look to an outfit. 

Move over man bun, the beanie is suddenly one of the coolest things that a man can sport today, and it’s here to stay!

Great for Bad Hair Days

It is rescue spelled with a capital R on a bad-hair day, without screaming it out to the world that you haven’t washed your hair in days. 

Suddenly, if all of those normally gorgeous locks decide to stick out rebelliously, the beanie styled right, is a godsend. 

Tuck your curls or tame your locks into temporary submission and no one will be any wiser!

The Sheer Variety Available

The beanie can be knitted from wool, made of silk or leather, and even homespun cotton. You don’t need to be in the dead of winter anymore to be able to wear a beanie. 

Anyway, whatever the material, the important thing here is how to wear a beanie such that one looks casually chic and absolutely ‘with it’ in terms of both comfort and fashion.

Choosing The Right Beanie 

You’ve finally agreed to get yourself a beanie. 

But how do you choose the right one that will suit your face shape and structure?

From designer boutiques and showrooms displaying the ultra-modern brand of the beanie to the man at the corner selling beanies knitted by his aunt, the beanie is suddenly just the thing to have to up the nifty look. Style-wise, there’s the cuffed beanie and the cuffless ones. 

And don’t get us started on the numerous prints and colors available!  

Based on Face Shape

Just like there is someone for everyone in this wide world, there is a beanie to suit every face. 

Thus, all you need to have is the perfect beanie to enhance your face and know how to wear it to catch all those second looks!

Now, buy a beanie that will accentuate the shape of your face and bring out your good features. 

Just as clothes must be styled to accentuate the figure, wearing a beanie means keeping a few basic pointers in mind. 

For round faces or noticeably square ones, choosing a beanie without a cuff that folds back, works. Wearing a beanie with a rib and with a looser fit also does the trick. 

The face appears longer and more angular if you wear a beanie this way. 

Do not cover the ears with the beanie. Instead, pull it back off your face to create that extra sharp look.

In contrast, if your face is long, wear a cuffed beanie that fits well. 

Call attention away from the length of the face by opting for detailing like stripes or color blocks. 

There’s nothing more simple or stylish than wearing the beanie as it should be worn. 

One important thing to remember when wearing the beanie is not to let it cover you up like a nun. 

Wear the beanie slightly pulled back and allow a little hair to show. 

Don’t cover the ears entirely unless you’re freezing to death. The front of the beanie should rest a little above the eyebrows. 

When you’re having a bad hair day, just fold back the beanie to create a neat cuff, and a little bit of the ears show.

Based on Hair Length

If you have short hair, wearing a well-fitted beanie would be just the thing instead of an oversized and slouchy beanie. 

Wearing such a beanie is a massive no-no since the balance of the head will be off, and you will only land up looking overwhelmed. A classic-style beanie and one that fits closely like the hipster will be perfect.

If you have gorgeous curls or sea waves for hair, a looser style of beanie looks trendy. A thicker type of fabric or wool in a slouchy beanie will allow some wayward curls to show, making it an elegant yet rakishly stylish option. 

While on the subject of hair, long-haired men should opt for a slim-fitted beanie. Wearing such a beanie will help balance out the long style of the hair and bring elegance into the frame. Wearing the beanie pulled back from the face creates the perfect look as it shows up the face and your best features.

Beanies to Avoid

The beanie might be one of the most stylish accessories a man can flaunt, but there are a couple of styles that any self-respecting adult man should not touch with a ten-foot pole. 


If you’re not a 6-year-old boy, and I don’t imagine you are, please stay away from beanies that are topped with pompoms, especially the type where the beanie is one color, and the pompom is another color, mostly a vibrant neon one!

While we don’t want to judge or cramp your street style, very few can pull off multicolored patterns with neon colors. 

That being said, the bobble hat beanie oddly has its roots in a traditionally male-dominated sector: the military. 

Yes, you read that right, the colorful bobble hat that you wouldn’t dream of wearing was once worn by battle-hardened soldiers. 

Specifically, regiments of the Scottish Highland branch of the UK army and Napoleon’s men were known for wearing these decorated beanies.

Baggy Beanies

Baggy clothes can work in some situations, that’s true. But the majority of the time, if you don’t have a great eye for fashion, you should avoid baggy garments.

That includes beanies.

A baggy beanie is not a good look for most people. While the David Beckham style can work for some people (and we’ll cover it later), generally speaking you should steer clear of an oversized beanie.

Unless you know what you’re doing, you’re just asking for trouble wearing anything that doesn’t fit you well.

Festive Beanies

Finally, we implore you to stay away from novelty beanies.

From the horrid contrast colors to those festive-looking beanies that come out of hiding during the holiday season, it’s not worth the risk.

Sure, it might match your ugly sweater for your annual ugly sweater Christmas party, but no one really needs a “jingle bell beanie”! 

Give Santa Claus back his color scheme and let the poor man do his job in peace, will ya?!

How to Wear a Beanie


You may live in a place battered with snow or blustery winds, or perhaps in a sprawling metropolis that has green matcha tea latte stands at every corner. 

Either way, why should you stick to headgear that is so old school or worse, so last season? 

Opting for a laidback or uber-stylish beanie, will keep you warm and still looking like your personal stylist spent hours getting the look perfect. 

Let it be our little secret that all you did was read this article and learned the inside info on how to wear a beanie the right way! 

There are many ways to wear a beanie, so let’s dive straight into it!

Straight Up

Nothing major here, just the straightforward, pulled-down beanie look that covers your ears. 

You might be like Steven Jobs and wear the same colored shirt every day because you’re cool, but there’s no excuse to wear your beanie straight up when there are so many better ways of doing it. 

If you do go this route, just make sure to choose a beanie based on our recommendations according to your face shape and hair length. 

An uncuffed beanie suits this style a tad more than a cuffed beanie. 

The Modern Working Man

If you have a long commute to work, or you go by foot, a beanie can be an excellent way to mitigate the morning breeze.

Nobody likes cold ears, so if you’re walking around with visible breath and cold hands, it’s probably a sign that you could benefit from wearing a beanie on your commute.

It might seem like a tall order to find a beanie that works with your work suit or formal outfit, but trust us, it’s possible. A classic cuffed beanie is probably your best bet if you’re looking for minimalist yet stylish.

Simply choose a color not dissimilar to those you’re already wearing, but perhaps a shade or two darker. 

The last thing you want to do here is draw unwanted attention upon yourself with a loud, brightly-colored beanie that takes away from your understated style. Unless, of course, fashion for you is all about expression and experimentation.

Generally, though, you can follow the standard rules fo men’s accessories. That is to say, if you’re wearing white sneakers a white beanie could be a good option. Likewise, if you’re wearing formal black dress shoes then perhaps a dark beanie would be your best option.

Just like with a belt, a pair of sunglasses, or a watch, you want to pay attention to your whole outfit if you want to give off the impression that you know what you’re doing when it comes to fashion.

The Fisherman Style

The fisherman was a smart guy. 

He first wore the beanie to stave off frozen ears from the cold weather out at sea. Not only did it keep his head warm, but it was also something to keep the hair off his face in all those windy seas.

That’s probably what gave rise to the fisherman’s way of wearing the beanie. 

Most modern men will not need to venture into the open stormy seas to catch a day’s worth of fish, but you can’t deny that the beanie is a fashionable way to keep one’s hair off one’s face while working. 

The fisherman’s way of wearing a beanie needs you to roll the beanie’s cuff twice, outward. Wear it with most of it towards the back of your head. 

This fisherman beaniestyle will check that wayward fringe while still allowing it to peek smartly out. 

You decide how much hair you want to show and adjust it accordingly, but don’t let too much of the beanie fabric slouch at the back. The beanie rests above the ears in this style.

This look is super in and is an indispensable part of the hipster look if you’re going for one. 

Wearing the beanie this way allows you to fall in with that snazzy street-culture look while using a relatively cheap and readily available accessory. 

The Robin Hood 

Another stylish way to wear a beanie is to bring back the Robin Hood look. Instead of cuffing the front, make a slight fold just at the ears. 

And for an absolutely care-a-damn look, bring the beanie right back until the material slouches near the nape. Hide the ears and allow hair in the front to show. 

Add to this a pair of casual linen trousers, and you’re ready for the weekend. 

The One Cuff 

Running to the store for supplies or picking up a coffee in your pants that you try to pass off as “athleisure”? 

This one’s for you!

Roll the cuff of the beanie once, and wear like you would the straightforward way. 

If it isn’t too chilly, let your ears peek out.

Don’t try too hard with this one, the point is to embody hashtag ChillVibes, instead of being that guy who tries too hard! 

Bending it like Beckham

David Beckham is like wine; he gets better with age! 

This style of wearing your beanie involves a super baggy beanie that you wear towards the back of your head, with the extra fabric creating a slouchy effect. 

Cover your ears but allow your hair to fall forward. 

Of course, only wear it this way if your hair is freshly washed and squeaky clean. 

No one wants to see greasy hair falling into your eyes! 

High Top, Up Top

Yes, you’re cool, and yes, you want a style to match that attitude. 

This style screams, “Too cool for school!”

Wear your beanie cuffed, towards the front of your head, with your ears exposed. The beanie will stand tall, almost vertical. 

This is an excellent way to give your face some height, especially if your face is round.  

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Frequently Asked Questions About Beanies

Should a beanie cover your ears?

Well, truth be told, it largely depends on the weather. 

If you’re freezing in the Arctic, it would be foolish to keep your ears uncovered. Safety naturally takes priority, and folding back the cuff to show one’s ears for style and elegance would be plain stupid.

However, if one has a choice and the chilly winds are not blowing you away, you can fold the beanie over to create a suave cuff that looks very snazzy. 

Are beanies in style in 2020?

Yes, they are! 

As a fashion statement that redefines casual chic, the beanie is here to stay. Though hat trends run from the simple to the ridiculously absurd, the beanie has taken a permanent seat on the fashion scene.

With their easy to produce, no-nonsense styling, wearing beanies has become the trend that is here to stay. They’re practical and can be worn by anyone to create effortless chic.

Is it rude to wear a beanie indoors?

The answer to this really depends on your levels of etiquette and the people you are with. 

Honestly speaking, the beanie comes under the category of a hat, and a hat must be removed when indoors. It comes under basic etiquette. 

One must be ‘uncovered’ as Shakespeare would have said when one is indoors. 

This is a marked sign of respect and began with the knights of medieval England when they removed their headgear as a sign of respect and trust.

A Final Word From The Trending Man

From everything that you have read above, one thing is crystal clear. 

The beanie is here to stay. 

If it has not left the fashion playgrounds of Paris and Milan or the runways of New York, one can safely say that it is still the most practical accessory that helps you blend in and stand out. 

Go forth and get yourself one of these, O knight in shining beanie, and get ready for all those second glances coming your way!

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The Trending Man

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