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How To Wear A Hat (Without Looking Like A Fool)

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When it comes to relationships, finding the perfect match can be as simple as swiping right. But as far as hats are concerned, ‘The One’ often proves annoyingly elusive. And that’s for those of us who are still actually trying to find it.

Most men – once bitten, twice shy – have resigned themselves to a quiet, hat-less life, their mates’ howling laughter still ringing in their ears after that one time with the ill-fitting straw trilby at the airport.

With seemingly endless styles to choose from, finding a hat that fits well, looks good and isn’t at odds with the rest of your wardrobe can be tricky. But chin up, because we’re here to run you through this season’s strongest headgear options, together with some simple tips and tricks to help pull them off.

The Fedora

What Is It?

The fedora is a hat, of course. But more than that, it’s headgear with history.

The fedora’s roots lie in the Greek word for ‘gift from God’, but it’s a style that has fallen in and out of favour since the late 19th century. In prohibition-era America, for example, it became synonymous with gangsters, whereas nowadays it’s more likely to be seen atop the bonces of raffish creative types, concealing a man bun beneath.

The fedora is distinguished by its soft felt construction, pinched front, teardrop-shaped crown and a wide brim that straddles the gap between a Stetson and a pork pie.

Who Wears It?

History is full of examples of men who harnessed the rakish flair of the fedora. During Hollywood’s golden age, class acts Cary Grant and Humphrey Bogart were rarely seen without one. In more recent times, however, the fedora has amassed a fan club that counts David Beckham, Jude Law and Tinie Tempah among its members.

How Do I Wear It?

The fedora gets a lot of flak. But done properly, one of these will instantly add some old-school charm to contemporary looks.

“A hat like this won’t work with jeans, trainers and a sweatshirt,” says Matt Hambly, head of content at menswear brand Spoke London. “Make sure you buy one that actually fits the way you need it to. If you want to wear it tilted back at a slight angle, James Bay-style, you may need to buy it slightly too small so that it sits snugly on your crown.”

Try it casually with a Cuban collar shirt and tailored trousers, or steer traditional with tailoring as a way to stand out from the rest of the suited crowd.

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The Baseball Cap

What Is It?

A true sporting icon, the baseball cap made its debut in 1860 atop the heads of Brooklyn baseball team the Excelsiors. Characterised by its protruding peak and rear fastening, it was originally manufactured to help shield players’ eyes from the sun.

Over the last 150 years, though, it’s been knocked right out of the park, coming to form a crucial part of the wardrobes of not only hip-hop royalty, but the modern hypebeast, too. And now – nestled neatly in the intersection between leisure and the rest of life – it epitomises high-low dressing.

Who Wears It?

The humble baseball cap might be camouflage for celebs seeking to go incognito on bad hair days, but those in the rap game have turned wearing theirs into an art form. Whether it’s BAPE, Palace or New Era, caps are now a style signature for the likes of Wiz Khalifa, Fetty Wap, Drake and Jay-Z.

How Do I Wear It?

Traditional curve-peaked caps that put a luxe spin on this sporty staple in suede, leather or wool can be worn with pretty much anything. Arguably the most on-trend way to work a baseball cap into your rotation, however, is as part of a casual outfit spliced with formal pieces like deconstructed blazers and Oxford shirts.

At the other end of the spectrum, the more streetwear-leaning styles like snapbacks and five-panel caps jar with trussed up gear, so wear them alongside overshirts and hoodies. Whatever style you opt for, just make sure yours is facing forward. And doesn’t promise to ‘Make America Great Again’.

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The Bucket Hat

What Is It?

With the return of all things ’90s over the past few seasons, it was only a matter of time before the style world mad was going madferit with Haçienda headgear once again.

The bucket hat’s return to fashion’s top flight is no mean feat, considering it wasn’t invented with looks in mind. Conceived in the early 1900s as a means of protecting Irish fishermen from the rain, it went on to shield the necks of troops in the ‘40s and during the Vietnam War.

However, it was with the mod movement of the ‘60s that the style found its stride, transitioning from a functional piece to a fashionable one. Despite falling in and out of favour in the decades since, the bucket hat has been worn by everyone from hip-hop royalty to Madchester lads, earning it some serious street cred.

Who Wears It?

In short: the brave. The bucket hat is the Marmite of the fashion world, which goes a long way towards explaining why only the boldest give it a go (think scumbro don Justin Bieber and NBA All-Star Russell Westbrook).

How Do I Wear It?

The bucket hat is firmly back on the streetwear scene, but you don’t have to be trussed up in a retro tracksuit (we’re looking at you, LL Cool J) to rock one. And, with all due respect to Liam Gallagher, you don’t have to be decked out in a parka to make the trend work either.

For a universally acceptable way to wear yours, allow the bucket hat to be the streetwear-leaning statement it has evolved into. Unless you’re actually going to a festival, pair it with stripped-back essentials (think classic T-shirts and summer knitwear) in muted colours.

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The Flat Cap

What Is It?

Often overlooked, the flat cap was once favoured by the English gentry – particularly those with a predilection for hunting and all-tweed-errrthing. More recently, in the nineties, it became the headgear of choice for wayward boyband members and old-timers whose sartorial prowess just wasn’t ‘what it used to be’.

Today, however, it’s all change. The flat cap has clawed its way back from the bog to earn a spot as one of the more unusually rakish pieces around, driven by outings of similar styles like the Newsboy in TV shows like Peaky Blinders.

Who Wears It?

No longer favoured solely by the likes of Prince Charles and his fellow septuagenarians, the flat cap now has its share of stylish flag-flyers, too – among them Cillian Murphy, David Gandy and Justin Theroux.

How Do I Wear It?

Despite its country connotations, the flat cap is surprisingly versatile, punctuating looks from smart-casual to smart perfectly.

In terms of fit, think along similar lines to the baseball cap, which shouldn’t be too tight or have too much excess fabric that could cause unsightly bunching at the top of your head. Too capacious a cap and you risk the mushroom effect. And getting roped into doing paper rounds.

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The Beanie

What Is It?

The beanie has – in some way, shape or form – been around since the 11th century. But, like so many other enduring menswear staples, the modern design we know and love has its roots in military and blue-collar uniforms.

Whether fisherman, crocheted or cable-knitted, the beanie is a sack of rugged, woollen (or cashmere, if you’re fancy) goodness that acts as the literal crowning glory to your outfit. Some even have pom-poms. (Don’t wear those.)

Who Wears It?

In times past, the beanie has almost exclusively been the preserve of out-of-work actors and ski-season brats. But thanks in no small part to Bill Murray’s turn as Steve Zissou in Wes Anderson’s The Life Aquatic, it’s a style that’s been given a new lease of life, since adopted by everyone from Jake Gyllenhaal to Liam Hemsworth.

The fact that brands like Virgil Abloh‘s Louis Vuitton and The Elder Statesman have given the beanie a luxurious makeover in recent seasons probably hasn’t done its rep any harm, either.

How Do I Wear It?

There are no hard and fast rules to pulling on/off a beanie, except that the Ashton Kutcher method (sitting sloppily on the back of your head) is an outright no-go.

“Balance a beanie’s casual leanings with structure,” says men’s style writer Luke Raymond, who has worked with the likes of ASOS and FarFetch. “Small fisherman types work well with formal overcoats. And think lighter weights for spring.”

We’d follow that up with: look in the mirror. If what you see is more roadman than ruggedly casual, then re-consider your options.

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The Panama Hat

What Is It?

Hats, as Gay Talese once said, can enhance one’s appearance. But you can’t just slap on any old lid and expect miracles. One of the trickiest styles to get right, but one with the biggest pay off if done right, is the Panama hat.

Originally known in the 17th century as the sombrero de paja toquilla (not to be confused with comedically large hats or Friday night shots), the Panama hat has a similar shape to a fedora with a central dent which is pinched at the front.

Despite the name, the origins of the Panama hat actually lie in Ecuador. As well as a change in name, this world famous head coverer has also changed in appearance. Traditionally only available in a bleached off-white colour with a black ribbon, today they can be found in all manner of shapes and colours.

Who Wears It?

A summer switch-up for fans of the felt fedora or homburg, the Panama hat was a firm fixture on the bonces of Paul Newman, Fred Astaire and JFK, who praised its lightweight, breathable qualities during the warmer months.

How Do I Wear It?

It’s just a hat, right? Like any of the styles on this list, you stick it on your head and be done with it. Wrong. When it comes to looking good, the Panama hat is less easy peasy lemon squeezy, more difficult difficult lemon difficult.

Firstly, you’ll need a style that suits your face shape. As a general rule that means opting for a larger brim if you have a round face, or a smaller brim if you’re of a smaller stature.

As for how to wear it without looking like The Man from Delmonte, make sure your outfit has a modern edge. That could be with a suit worn as separates and dressed down by simple basics for a casual summer wedding, or with an Oxford shirt slipped under a suede jacket. And avoid all-white tailoring at all costs, obviously.

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