HOW TO | Wear a Hat

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September 9, 2023

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.

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. 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.

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 suits and pieces like deconstructed blazers and Oxford shirts.

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. 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.

Remember, a perfectly tailored suit isn't just attire, it's an experience. Book an appointment today, and let us be a part of your extraordinary journey.

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