How to Wear A Beanie 3 Different Ways (Casual, Work, Special Occasions) · Effortless Gent

Are you a fan of beanies, but feel limited as to where you can wear them or keep them on? Guess what, times have changed! We live in a new world where beanie rules and guidelines are much less strict than in years past.

What this means: Yes, you can still wear beanies casually, of course. But you can also wear them during special occasions, to the office, with a suit, even with a tuxedo(!)

Sound crazy? Totally true, but of course, the devil is in the details. In this post, I’ll discuss the various occasions in which it is now appropriate to wear a beanie along with examples of types of beanies to wear in each setting.

Have that Chase Sapphire handy, because by the end of this, you’ll be checking out on any number of these beautiful headpieces.


A Bit Of Beanie History

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The beanie has roots all the way back to the 12th century as a monmouth cap primarily for soldiers, but modern beanies as we know them came about in the early 20th century.

They were originally favorites of the working class, providing blue-collar laborers with warmth and protection in some of the most labor intensive jobs.

By the 1940s, baseball hats were all the rage, pushing the wool caps out of the mainstream. But the humble beanie found a home among the college students, hippies and beat poets who ran the counterculture movements.

Soon they started to make their way back into the mainstream. Sporting events, casual outings, cold weather, etc. called for beanies. And brands have gotten really creative with beanies recently, releasing versions in different cuts and colors, making it easier to wear in more dressy situations.

Let’s talk through 3 different scenarios you can wear a beanie today, and as we’ve been trying to hammer home, it’s not just for casual situations or outfits anymore.

How To Wear A Beanie In Three Different Settings

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So as we mentioned, beanies were once relegated solely to dressed down situations.

But with the general casualization of men’s styles over the years and the acceptance of a casual / smart casual dress code at the office, there are more and more places where you can wear a beanie (and not feel weird about it).

Here are three specific examples!

Casual Settings

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Beanies are in their element in a casual setting. They are the proverbial cherry on top for any cold weather outfit.

Whether you are wearing a sweatsuit to the corner store to grab a couple last minute ingredients for a cozy fall dinner, or you’re in jeans and a hoodie going to the movies, a beanie will fit right in.

You can wear them to run errands, to sporting events, parties, and more. When the temps border on freezing, you can wear a beanie. There are no special rules to follow here.

Beanies of all colors, patterns, cuts, and logos will work in a casual setting. You just have to find what works for you and what you like best and you’re off to the races.

Here are a few we can recommend:

Carhartt Beanie

Classic, simple, and tough as nails. For $20 or less, this Carhartt beanie can be the only beanie that you own. The classic workwear staple can be found in a million colors.

Carhartt Beanie

“This men’s acrylic watch hat is made of stretchy rib knit that’s soft to the touch and finished with a Carhartt patch on the front.”

Shop Amazon

If there is a color you want for a specific outfit, you can find it. It’s thick enough to keep you warm all winter long and they’re eternally cool.

Arc’Teryx Bird Head Toque

We love a GORP-y option. Arc’Teryx had a moment a few years back when you couldn’t scroll Instagram without seeing hoards of teenage boys wearing the Arc’Teryx shell jackets.

That noise has since cooled off, but the brand is still as good as it ever was. This beanie isn’t exactly for those looking for an understated piece. This can be the pop of color that your outfit needs.

San Francisco 49ers Beanie

A lot of men’s fashion guys don’t believe that men should bring sports into your personal style, to which I say, they don’t know what they’re talking about! Sports are part of the big picture, and if you have an allegiance to a team, then get a beanie.

Clothing should tell stories, and if loving a certain team or wanting to show loyalty to your alma mater is important to your identity, then a beanie is one of the most tasteful ways to do it.

Levi’s Slouchy Red Tab Beanie

Yes you can cop a hat from the jeans store. This little $20 beanie is perfect for the holidays with a fair isle pattern.

You can swap out the ugly Christmas sweater with a much cooler beanie.

Supreme Snowman Beanie

Okay, bear with me, but this is incredible. For one, it doesn’t get more festive than this. Also, I own a couple of Supreme beanies, and they are thick enough to last you through another ice age.

Supreme Snowman Beanie

“This acrylic cuffed beanie with jacquard knit graphic at crown + logo at cuff makes a perfect winterland statement bringing both mirth + glee to all those surrounding you.”

Shop Supreme

If you want to go with a streetwear look, this is the best beanie you can snag for the winter months.

Business Setting: Non Formal / Creative Offices

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Beanies just became acceptable to wear to work within the last few years. If you’re not in an office where you need to wear a suit, you can probably wear a beanie. 

If you’re wearing it more for utility than fashion (even though, since you’re reading this, the latter is more likely), it won’t appear sloppy.

You may want to take it off when you get to the office, but most workplaces are so casual these days, you shouldn’t have a problem wearing the beanie as part of your outfit. 

The key here is contrast, balancing casual with more formal elements. I like to make sure I am wearing well fitting trousers or denim with a long sleeve shirt or a sweater on days that I decide to wear a beanie. 

For example, when I’m wearing a beanie at the office, my ideal fit is a pair of black wool trousers with either minimal sneakers or loafers, a long sleeve collared shirt—usually a striped shirt from J. Crew or Brooks Brothers—occasionally a cardigan sweater over it, and a minimal beanie. 

You’ll want to avoid big logos, inappropriate designs, or slogans. Remember to keep it on the modest side; wearing a beanie to the office wasn’t always seen as acceptable. 

So go minimal, and keep it extra sharp with the rest of your outfit. Since you’re wearing a casual accessory, you’ll want to offset that with dressier clothes.

Here are some examples of more minimal, office-friendly beanies:

Acne Studios Beanie

One of the most recognizable beanies in the clothing industry. Acne Studios robot-like face logo is one of the most tasteful logos in the high fashion world.

At $140, the beanie is a bit pricier compared to some of the others on this list, but if you grab it in a classic color like black or gray, you’ll be able to wear it forever.

The brand equity is through the roof and you’ll instantly be one of the coolest kids in your office.

Madewell Wool Knit Beanie

J.Crew offshoot Madewell has been one of the hottest recent newcomers in the menswear space for good reason. They are masters in contemporary, subtle elegance.

Their beanie lineup is no different. Sporting a clean, minimal design and made of merino wool, this is a great option if you’re going to be wearing it in the workplace.

Special Occasions: Holiday Dinners, Parties, and “Creative” Formal Events

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Wearing a beanie for special occasions is a professional maneuver, but with the proper guidance, can be pulled off by just about anyone. 

The best example of this would be Mahershala Ali at the Academy Awards. He wore a beanie at a black tie event and just about every media outlet ate it up. They loved it. 

Go with a beanie that has elevated details, and stick to brands known for producing top notch wool garments.

If you’re wearing a tie, choose a beanie that’s either in the same color family (a sky blue beanie with a navy tie) or a complimentary color (a yellow beanie with a navy tie).

man wearing navy suit with yellow beanie standing in busy street

In most cases, however; you’ll want to stay with a classic color. Make sure to minimize other accessories as they could potentially make the entire ensemble appear more casual overall.

Here are a couple beanies that fit the bill:

Asket Ribbed Wool Beanie

Asket is one of my favorite brands for affordable basics. Their Ribbed Wool Beanie is the perfect go-anywhere, do-anything beanie and it’s only $50.

If you’re going to wear a beanie with a full three-piece suit or your finest evening wear, topping off your outfit with this Asket will not raise any questions from the fashion police.

Todd Snyder Italian Recycled Cashmere Beanie

I couldn’t finish this list without including a cashmere piece. Cashmere is the fabric of the gods.

Lightweight, yet still perfectly cozy, Todd Synder makes recycled cashmere beanies, so you can sleep well at night knowing that it’s better for the environment than regular cashmere.

This is one of my favorite beanies in the current market because it perfectly combines elegance with utility.

Brave Enough To Wear A Beanie Now?

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Beanies are a staple of any stylish man’s wardrobe. What once started as a cap of protection for the blue-collar working man has turned into a stylish icon, suitable for any occasion.

You can wear them anywhere nowadays, from casual outings to creative black tie affairs. 

Wear them to keep warm, to provide a pop of color, or just to show support for your favorite team. The rules are more lax these days!

Enjoy your fuzzy, wool headpiece in peace!

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