When it comes to relationships, finding the perfect match can be as simple as swiping right. But as far as hats for men 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 hat 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.