Winter Topper: How To Wear A Beanie With Style

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.


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.

Paddy Maddison

Paddy Maddison is Ape's Style Editor. His work has been published in Esquire, Men’s Health, ShortList, The Independent and more. An outerwear and sneaker fanatic, his finger is firmly on the pulse for the latest trends, while always maintaining an interest in classic style.