How To Wear A Beanie Without Looking Like An Idiot

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The cold-weather headwear landscape is a notoriously tricky area to traverse. Beanies for men are the only vaguely acceptable option and let’s face it, they’re hardly held in high regard by followers of fashion.

However, as is the case with so many things in the world of style – it’s not just a matter of what you wear, it’s also about how you wear it. And with that reasoning very much in mind, we’d like to take to the stand in defense of one of winter’s most misunderstood accessories.

 

If you’ve ever uttered the words, “Why do beanies look bad on me” it may be because you’ve simply been wearing the wrong ones. Beanies work well with menswear’s current love of utilitarian workwear, and there are several styles to match even the weirdest and lumpiest of face shapes. We’ll explain all about how to wear a beanie the right way shortly. 

Key Takeaways

Navigating the world of beanies without committing a fashion faux pas can be challenging. The Carhartt Acrylic Watch Hat stands out as a prime example of how to get it right and how to look good in a beanie. . Known for its warmth and durability, especially during harsh winters, it’s designed to be both functional and stylish. Its classic design aligns perfectly with the workwear trend, ensuring that wearers look intentional and put-together.

The North Face Salty Beanie, designed for the Fisherman style, is perfect for extremely cold conditions. It fits snugly, looks stylish, and is of very good quality. This beanie showcases that even a functional, durable hat can be worn stylishly.

Lastly, the SEALSKINZ Water Repellent Cold Weather Bobble Hat brings a touch of style with its pom-pom design while ensuring your head remains dry and cozy in rainy, snowy, and muddy conditions.

All these hats are excellent examples of wearing this accessory with confidence and style. Whether you’re going for a classic look with the Carhartt, a snug fit with the North Face, or a stylish yet functional design with SEALSKINZ, there’s a beanie out there for everyone.

man carrying his bike
isto.pt / Instagram

How To Wear A Beanie: The Ultimate Guide For Men

These failsafe winter hats belong in every guy’s wardrobe, but how exactly should men style beanies? There are several ways to do it, and here are a few of our favorites. 

1. The Classic Cuffed Beanie

Carhartt Knit Cuffed Beanie

When you hear ‘woolly hat’ this is most likely what you think of – and there’s a good reason for that. This style is one of the most popular and versatile in existence and has been championed by hip-hop royalty, workmen, and everyone else in between.

As far as beanies for men go, this is the grandaddy.

How to wear a beanie
Jacob Hilton on Unsplash

2. The Fisherman Beanie

THE NORTH FACE Salty Lined Beanie

It may have become the hipsters’ cold-weather headgear of choice, but don’t let that put you off. Styled as part of a workwear-inspired look, the fisherman beanie really comes into its own.

This miniature woolly hat features a turn-up and sits on top of the head, ending just above the ear.

How to wear a beanie
Michael Benz on Unsplash

3. The Bobble Hat

SEALSKINZ Water Repellent Cold Weather Bobble Hat

A pom-pom isn’t exactly the manliest of decorative details, so it may come as a surprise to learn that it actually has its roots in the military. Napoleon’s infantry and the Scottish Highland regiments both used pom-poms on their hats to differentiate between companies and today it is still possible to wear one without looking like a carol singer.

Steer clear of neon colors, overly festive patterns and anything with more than one modestly-sized bobble.

Photo by Haran Amorim on Unsplash

How To Choose The Right Beanie For Your Face

“A beanie is a great staple of your winter wardrobe,” says Sarah Gilfillan, stylist and founder of SartoriaLab, a London-based men’s styling service. “But before you head out to buy one, remember that small details can make the difference as to whether or not the style suits you.”

If you’re round or square of face, avoid designs that will make you look like Harry from Home Alone. “Choose a beanie without a turn-back cuff, with ribbing and a looser style that can add a bit of height to your face,” suggests Gilfillan. “Also, wear it slightly back off your face rather than pulling it down over your ears.”

A bobble hat is another good option for this, but steer clear of anything too ‘out there’. You don’t want to look like Kevin, either.

If you have a longer face, a beanie can work nicely. “Opt for a turn-back cuff, which could even be in a contrasting color or have stripe detailing,” says Gilfillan. “Wear a tighter fitting style that sits snugly on your head to avoid adding any more height.”

FAQ
    • Do beanies look good on men?

      Newton’s third law of headwear: for every nice hat, there is an equal and opposite crap hat. And while beanies look great on men when worn correctly, there are some styles every guy should avoid. Here’s what to look out for when it comes to beanies for men.

      • What beanie styles should men avoid? 

        1. The Baggy Beanie

        As mentioned earlier, for several years in the noughties, every man and his dog was wearing an oversized, slouchy beanie. Needless to say, it was not a good look.

         

        David Beckham, as he often is, was instrumental in the spread of this fad. The former England captain was constantly getting papped wearing his baggy beanie in airports the world over, leaving us all asking the same question: just what exactly was he trying to smuggle through customs?

        beanies for men
        Christopher Burns on Unsplash

        2. Visor/Peaked Beanies

        If a 13-year-old kid in an oversized Limp Bizkit T-shirt and baggy jeans thinks it’s ‘sick’, the rest of us should probably leave it well alone.

         

        Unless you’re a badly rendered computer character called ‘Otto’ in a Nintendo 64 snowboarding game, this headwear nightmare is best given an extremely wide berth.

        3. Novelty Beanies

        You should really know by now that in the world of menswear, anything with the prefix ‘novelty’ should be avoided like the plague, and beanies are no exception.

         

        If you stumble into a ski shop and spot a fleecy hat, decorated with a blue furry mohawk, turn swiftly around, walk out of the door and never return. That’s just common sense

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