How to Wear a Beanie for Men: The Ultimate Guide

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This article talks about the ubiquitous beanie and how to wear it in a variety of styles that will complement your face and personality. But before we dive in, I’ve got something important that I 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 a thought about the latest trends? Me neither!

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 get difficult 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 I tell you all about how to style your beanie to suit you, if you’re anything like me, you’ve probably had that niggling thought about why it’s called 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 has it 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 me 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. Nothing simpler or smarter than wearing the beanie right. 

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 so that a neat cuff is created, 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 a beanie that is big and slouchy. Wearing such a beanie is a huge 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 style 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 I’m not one to judge or cramp your street style, very few can pull off multicolored patterns with neon colors. 

Also stay away from those festive looking, novelty beanies that especially come out of hiding during the holiday season. 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, my poor guy, 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! Let’s dive straight into it, then!

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 must though, 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 Fisherman Style

The fisherman was a smart guy. He first wore the beanie to keep out the cold. 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 cuff of the beanie twice, outward. Wear it with most of it towards the back of your head. This style 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 easily 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 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 a good way to give your face some height, especially if your face is round.  

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

Our detailed review has been contributed to by multiple members of The Trending Man Review Team to ensure the best research and highest standard of quality. Have a good or a bad experience with one of the products? Please let us know, we love the feedback!

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