The cold-weather headwear landscape is a notoriously tricky area to traverse. Beanies are basically the only vaguely acceptable option, and let’s face it, they’re hardly held in high regard by followers of fashion. You can’t really blame them either. After all, any time these woollen warmers have strayed into the public fashion consciousness for longer than five minutes there have been terrible, terrible consequences.

For example, David Beckham and his legions of style disciples spent the best part of the noughties proudly rocking a look that said, “I’ve got a turd in my hat”; and during the first coming of Craig David, the R’n’B/Garage crossover crooner exemplified perfectly why condoms should always be rubber and worn on your penis, as opposed to woollen and worn on your head.

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 defence of one of winter’s most misunderstood accessories.

If you’ve ever uttered the words, “Hats just don’t suit me” it may be because you’ve simply been wearing the wrong ones. In the world of beanies, there are a number of styles to get to grips with and something to match even the weirdest and lumpiest of face shapes.

Picking 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 personal 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 colour or have stripe detailing,” says Gilfillan. “Wear a tighter fitting style that sits snugly on your head to avoid adding any more height.”

Beanie Styles To Embrace

To keep your ears warm in style, these are the beanies you can rely on. Stick to these iterations and you can’t go far astray.

The Classic 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, winter workmen and everyone else in between.

As far as beanies go, this is the grandaddy.

A classic cuffed beanie for men

The Fisherman 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 wooly hat features a turn-up and sits on top of the head, ending just above the ear. Just make sure not to get one any smaller, unless you’re planning on wearing it to a Bar Mitzvah.

How to wear a fisherman's beanie

The 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 colours, overly festive patterns and anything with more than one modestly-sized bobble.

How to wear a bobble hat for men

Beanies To Avoid

Newton’s third law of headwear: for every nice hat, there is an equal and opposite crap hat. Here’s what to look out for.

The David Beckham Airport Turd Smuggler

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 in there?

David Beckham oversized beanie

Visor/Peaked Beanies

If a 13-year-old kid in a 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 badly rendered computer character called ‘Otto’ in a Nintendo 64 snowboarding game, this headwear nightmare is best given an extremely wide berth.

Peaked/Visor beanie for men

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.

Men's novelty bat beanie

How To Wear A Beanie

Here are a few fail-safe ideas on how to style a beanie, along with the best versions you can buy to achieve each look.

Commuter Beanies

Just because you need to dress a little smarter than usual, it doesn’t mean your loaf of bread should have to suffer the cold.

A traditional cuffed beanie is your best option here, although a bobble hat can also work so long as you opt for subtle, neutral colouring. Grey, black, brown and navy are safe and work-appropriate options – you don’t want to rock up to the office looking like a Belisha beacon, after all.

Consider texture mixing too. Adding another piece of knitwear into your commuter outfit can ensure you don’t look like another office drone. Try wearing your beanie with a flannel suit and wool overcoat or a knitted roll neck for something a bit more business casual.

How to wear a beanie with a suit for men

Selected HommeH&MJ.CrewWhistles

Acne Studios

If the thought of spending over £100 on a woolly hat doesn’t make you shudder, Acne Studios is a good shout. The Swedish label has a longstanding reputation for its typically Scandinavian, minimalist aesthetic and the superior quality of its materials.

You can expect these traits in abundance when it comes to the brand’s beanies, along with its instantly-recognisable straight-faced emoji detailing.

Buy Now: £110.00

Acne Studios beanie

Topman

You can always rely on Topman to deliver the goods, no matter what you’re looking for. Beanies are no different and the variety on offer is nothing short of dizzying.

The high-street favourite is well-known for providing the masses with a mixture of both timeless and trend-led products at affordable prices.

Buy Now: £12.00

Topman beanie

Norse Projects

Danish streetwear/casualwear crossover label Norse Projects perfectly encapsulates everything there is to love about Scandinavian fashion. The brand’s seasonal collections consistently straddle the line between timeless and contemporary and the beanie is one of its staple pieces.

Both the classic turn-up beanie and fisherman beanie have featured heavily in Norse’s collections and can be instantly recognised by their signature white-on-black, woven branded patches.

Buy Now: £50.00

Norse Projects beanie

Moncler

Granted, Moncler’s beanies aren’t exactly cheap, but bloody hell do they look good. The Italian alpine sportswear label has built a reputation as one of the coolest names on the slopes and its hats are some of the finest around.

Woven from the finest wools and punctuated with the iconic Moncler tricolour branding and signature felt tab – if you’re looking for some headwear that screams ‘luxury’, this is it.

Buy Now: £110.00

Moncler beanie

Streetwear Beanies

Across the majority of menswear genres, it’s fair to say that the beanie’s popularity has – at best – fluctuated. However, in the world of streetwear, it’s appeal has remained very much steadfast. Alongside hoodies, trainers and baseball caps, beanies are one of the true streetwear staples.

As far as colours are concerned, pretty much anything goes. The key to getting the look right lies in the branding and graphics. So much of streetwear culture is about what labels you’re wearing. If you’re stunting like the kids who camp outside Supreme and Palace drops, you’re halfway there.

Go for raw, relaxed-fit denim, a hoodie layered under a coach jacket, then simply top it off with one of the brands below and you’re good to hit the streets.

Men's street wear beanies - how to wear

ASOSBerkshaBoohooH&M

Noah

If you find streetwear a bit puerile, Noah may well be the label to change your mind. The brand is the brainchild of former Supreme creative director Brendon Babenzien and is probably best described as ‘streetwear for grown-ups’.

If you’re a bit apprehensive about wearing anything too heavily branded, or with graphics that are a bit too eye-catching, Noah’s clobber is a safe bet. The label always has a few chunky knit beanies in its collections.

Buy Now: £30.00

Noah beanie

Stussy

If it hadn’t been for Shawn Stussy’s eponymous California-based surfwear label, would streetwear as we know it today even exist? Perhaps not.

Stussy was founded all the way back in 1980 and is often credited with being one of the brands that spearheaded the movement. As a result, its logo is one of the most recognisable. If you were after a beanie with some serious street heritage behind it, you need look no further.

Buy Now: £45.00

Stussy beanie

BAPE

A Bathing Ape (often abbreviated and stylised as BAPE) is one of the biggest labels on the streetwear scene. Its founder, Japanese DJ and fashion designer Nigo, is one of the most respected names in the game and his clothes have a reputation for stirring up immeasurable levels of hype.

BAPE is known for its bold camo prints and striking graphics, as well as its iconic ape head logo. Beanies are one of the brand’s key items and former head honcho Nigo can often be seen rocking one himself.

Buy Now: $79.00

BAPE beanie

Patta

Originally founded as a multibrand streetwear store in Amsterdam in 2004, Patta developed its own line of T-shirts and hoodies that were initially only intended for staff, friends and family. However, as the store’s reputation spread it became clear there was a demand for an in-house label.

Today the brand is at the core of the Dutch streetwear scene, as well as having a strong global following. Expect bold branding, vibrant colours and a healthy dose of Dutch street steez.

Buy Now: €30.00

Patta beanie

Workwear Beanies

The obsession with workwear in men’s fashion has been going on for a long time and it shows no sign of letting up. Woolly hats are one of the look’s key accessories, but there’s a right way and a wrong way of doing it.

The fisherman beanie is the style best suited to this rugged, outdoor aesthetic and a classic turn-up beanie can work too. To get it right, you’ll want to opt for something with little to no branding in a block colour, styled with some heavy duty denim, work boots, a flannel shirt and chore jacket.

Whether you’re felling trees in the Yukon, or just heading for a half a pint of craft ale in Dalston, go to work with one of these key brands below.

How to wear a workwear beanie or fisherman's beanie

Selected HommeWhistlesSimonsPrimark

Carhartt

You can’t think of workwear and not think of Carhartt. The American label has been doing its thing for well over 100 years and has kitted out everyone from mud-covered farm workers to European cool kids in the process.

Expect rugged quality, good looks and plenty of heritage appeal.

Buy Now: £16.65

Carhartt beanie

ASOS

OK, so ASOS isn’t exactly a well-established workwear outlet, but it certainly has the right tools. The online retail giant stocks a huge selection of own-brand beanies, but its fisherman styles are particularly handy when it comes to the workwear look.

With a wide range of colours and prices that will leave you with change from a tenner, it’s hard to complain.

Buy Now: £10.00

ASOS beanie

Patagonia

If you want to save the planet and look good at the same time, Patagonia will be right up your street. The California-based label has its roots in outdoor pursuits and prides itself on being environmentally sound.

What’s more, it makes some quality beanies from hardy materials that are more than capable of taking whatever you or the weather decides throw at it.

Buy Now: £29.99

Patagonia beanie

BoohooMAN

For up-to-date fashion at bargain prices, BoohooMAN is a solid choice. The site has a huge selection of hats to choose from, but when it comes to perfecting the workwear look, its Docker hats are what to add to your basket.

Featuring a ribbed texture, undersized fit and turn up – this workwear classic is the perfect way to put a lid on your look.

Buy Now: £8.00

BoohooMAN beanie

Winterproof Beanies

When the cold really sets in, let’s be honest, a tiny fisherman beanie isn’t going to cut the mustard. To really keep the chill at bay you’re going to have to go all out. We’re talking special cold-weather fabrics, fleece linings and brands that were built for the outdoors and not, say, Instagram.

Simply get layered up with your thermals, parka and snow boots and then finish with one of the brands below to battle the elements in style.

The best winterproof beanies for men

SimonsGapWoolrichH&M

Canada Goose

When it comes to outerwear built specifically to stand up to the harshest of conditions, few are better known than Canada Goose.

The company’s beanies may be a bit over budget for some, but if you really want to stay toasty in sub-zero conditions, it’s well worth splurging the extra cash.

Think superior protection from the cold, rugged build quality and iconic Canada Goose badge branding.

Buy Now: £125.00

Canada Goose beanie

The North Face

California-based outdoor specialist The North Face has kitted out many a polar expedition, so you can put your full trust in the brand when it comes to keeping your head warm when winter bites outside the Arctic Circle.

The bonus with North Face gear is that it looks great too. So, even if the only expedition you have planned is to walk the dog after dark, a beanie from this legendary label will still be more than suitable.

Buy Now: £20.00

The North Face beanie

Woolrich

Companies such as The North Face and Canada Goose may be the ones outfitting the arctic explorers of today, but back in the early years, Woolrich was the brand carrying the torch.

The Pennsylvania-based outerwear label kitted out Richard E. Byrd’s 1939 Antarctic expedition, as well as supplying clothing for the American Civil War. If you’re looking for warmth, quality and heritage, you’ll not find any better than this.

Buy Now: £70.00

Woolrich beanie

Fjallraven

Swedish outdoors outfitter Fjallraven may be best known on these shores for its Kanken rucksacks, but back on its home turf and with outdoor enthusiasts the world over, its wider outerwear line is held in very high regard.

For a technical winter hat, guaranteed to keep the cold away and injected with a dose of Scandinavian styling, look no further.

Buy Now: £45.00

Fjallraven beanie