Life Skills

9 Ways To Wear A Beanie Without Looking Like A Teenager

  • Nov 1, 2023
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9 Ways To Wear A Beanie Without Looking Like A Teenager

The beanie, surely one of menswear’s most polarising accessories. For some, it’s a quick and effective way to change up a look. For others, the unpleasant image of David Beckham’s comically oversized woolly hat that’s been seared into their memory since 2004 makes it impossible to take the idea of wearing one seriously.

For those who fall into the latter camp, we understand and empathise with your beanie-related reservations. However, we’d urge you to reconsider your position when picking out your next piece of winter headwear.

For all its misuse and bad styling, the beanie is actually a very useful tool in a man’s sartorial inventory. The real problem here is that most people just can’t figure out how to wear one. With that in mind, we’ve outlined a few key ways to style this divisive breed of hat that’ll give even the most ardent of naysayers pause for thought.

The Beanie Styles To Try

There are some very deliberate omissions from the list below, most of which had their day in the 2000s. Remember David Beckham’s oversized and loosely worn beanies that resembled something the seven dwarfs would wear? Don’t do that. Or the Craig David-style headwear that looked like the biological leftovers of a circumcision? Don’t do that either. Instead, stick to the time-honoured beanie styles below.

Cuffed Beanie

The classic woollen beanie worn down over the ears and cuffed all the way around. You can’t really go wrong here: pick a wearable, evergreen colour and as little adornment as possible and you can wear it with almost anything.

The Fisherman Beanie

Chunkier, ribbed and a more directional look these days, the fisherman beanie was originally worn by men shivering on the decks of fishing trawlers and naval frigates.

Today, it’s worn by workwear-loving urbanites a little shorter than a regular beanie. Still cuffed, it usually sits a little above the ears.

The Bobble Hat

If it works for McCauley Culkin, it works for us. The bobble hat may have slightly juvenile connotations but it originated in the military and works well in the depths of winter.

Avoid anything overly festive or novelty (a rule for life right there) and look for cable-knit styles, subtle Fair Isle designs, or something plain.

The Right Beanie For Your Face Shape

The natural, dome-like shape of a beanie can accentuate your jawline and the general shape of your face, so it’s imperative you pick the right style.

If your face is round, a beanie might not be the best style for you, although ribbed designs and bobble hats would give the appearance of length. Similarly, if you have long or narrow features, a chunkier style with a larger cuff will add a little width and proportion.

9 Stylish Ways To Wear A Beanie


At its core, the beanie is a casual accessory. So no surprise then that one of the easiest ways to style it is as part of a casual outfit. Paired with off-duty staples like hoodies, jeans, T-shirts and laid-back outerwear, this woolly warmer really comes into its own.

The first thing to consider is the hat itself. Generally speaking, smaller styles are the best way to go. A mini roll beanie that sits about halfway down the ears is a safe bet.

Colour-wise, a lot will depend on the rest of your outfit. Think navy, charcoal or black for maximum versatility, perhaps in a flecked wool to add a dash of interest. That’s not to say anything brighter is out of the question, just be sure that there isn’t anything else vibrant in the outfit fighting it for attention.

Moving further south, stick to casual outerwear staples like bomber jackets, parkas and overshirts, paired with weekend-friendly legwear. For the footwear, opt for something relaxed and suede – a chukka boot would work well – or canvas and minimal.


Were you to be forced to stock your entire wardrobe with garments from a single subgenre of menswear, there would be much worse choices than workwear. Rugged, versatile, timeless and comfortable, we could wax lyrical about its virtues all day.

As luck would have it, beanies just so happen to be an integral part of this aesthetic’s winter lineup. The key style to consider here is the fisherman beanie; an undersized variation with a single roll that sits just above the ears.

It’s a classic piece of workwear headgear and a great alternative if you’ve decided traditional beanies are not for you. Stick to dark colours and ensure the knit is thin enough so that it doesn’t force your ears to stick out. (Never a good look.)

In terms of the outfit, here are three words to live by: overshirt, jeans, boots. These pieces are three of the cornerstones of workwear and can be called upon, again and again, season after season. Again, keep colours generally dark, but don’t be afraid to go for a bold block colour where the overshirt is concerned. Royal blue is the classic choice.

Smart Casual

There was a time not so very long ago when wearing a beanie with any sort of tailoring would have been unthinkable. In recent years, however, we’ve seen that it can be done in a stylish manner. Just look to the sartorial stylings of male model Richard Biedul for proof.

The trick here is to keep things on the relaxed side of smart and use the beanie to dress things down further still. This is no time for vibrant colours, though, so keep the headwear subtle and neutral in tone. Grey, navy or black if you want to play it safe; burnt orange, burgundy or brown for something a little more seasonally relevant.

Mix and match smart staples like dress trousers and black leather shoes with casual cold-weather essentials like roll neck jumpers and knitted polos. Layer with some smart outerwear – something like a wool overcoat – and use the headwear to bring the look together.

Winter Ready

There comes a point every year when wearing some sort of warming headwear becomes unavoidable. For many, this means reluctantly donning an unsightly fleece-lined tea cosy while braving the morning commute. Style simply doesn’t come into it. The way we see it, though, is that if you have to wear it, it might as well look good.

Loose the ill-fitting woolly hat and shop instead for something more streamlined. For maximum warmth and comfort, look for options made from merino wool, or even a cashmere blend if you’re willing to pay a little more. In terms of colour, stick to the winter theme. That means darks, neutrals, blues or earthy autumnal tones.

Team the beanie with a true winter coat, heavy-gauge knitwear, seasonally-appropriate legwear and some sturdy boots for best results.

Knits & Texture

Mastering texture is one of the pillars of good dressing. Tactile fabrics can add depth, create subtle focal points and really elevate a look to the next level. Headwear can play a role in this, too. Start thinking of it as a fully integrated part of your outfit, as opposed to something that just gets plonked on top.

Opt for a ribbed beanie for maximum texture and go for a colour that really allows the fabric to speak for itself. Lighter colours like grey and cream are good at this but darker shades in flecked wool work nicely too.

Use other textured pieces to enhance one another. A chunky knitted sweater will match the hat, while wool, suede or shearling outerwear creates contrast within the look. Textured wool trousers are a winter favourite and look the part with anything from Derby shoes to luxe sneakers.


There are endless ways to style a beanie with outfits inspired by hip-hop, sportswear or designer streetwear. You’ll find more colours and overt branding at this end of the market, but simple black beanies also work to anchor a look with oversized outerwear, big prints or statement hues below the neck.

The reverse is also true. Wear a bold beanie with a simple black hoodie or puffer jacket. Of course, this is no-holds-barred menswear so clashing patterns and colours can also work.


Cold mornings en route to work are another time when a beanie is a practical necessity and not just a stylish accessory. They work well with modern officewear, whether your workplace leans smart or casual. Just pair your headgear with your outerwear.

A fisherman style works best with chore jackets, truckers and duffle coats, while a simpler beanie is better suited to an overcoat or puffer.

If you wear headphones on the way to work, make sure your hat fits over them comfortably or vice versa.

The Great Outdoors

Hiking gear has fully infiltrated everyday menswear and doesn’t look like packing up its tent any time soon. With fleece tops, trail shoes and technical rain jackets all in the regular rotation, adding a beanie is an authentic way to top the look.

How specialist you go here will depend on whether you spend your weekends yomping in the wilderness or dog-walking round the local common. If it’s the former, look for elasticated linings and fleece linings to keep the worst of the elements at bay. If it’s the former, there aren’t a huge number of rules: you’ll get away with more colour, pattern and branding so long as the colours coordinate.

With A Suit

Ok, this look is probably as divisive as Brexit and there may well be more sceptics than advocates. But these are the days when the traditional rules of tailoring have been torn up and are fluttering somewhere in the wind. There are, we believe, two ways to wear a beanie with a suit.

You can go tonal, pairing something like an off-white hat with a grey suit, or a navy suit with a hat in a different shade of blue. Alternatively, there’s the peacock option where you wear a beanie as a pop of colour (yellow, orange, green) to offset the formality of a suit or separates. In either case, go for a slightly thick material for the hat.

Disclaimer: This story is auto-aggregated by a computer program and has not been created or edited by menshealthfits.
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