Hats on men can be… tricky. But think back, past the awkward phase of Redditors in fedoras, to the glory days of Sinatra, Grant and Jones (Indiana, that is), and you might well be inspired to give them a shot. As well you should. 

Between classic Panamas and designer snapbacks, caps in premium cashmere and luxurious beanies, the best hats for men come in more styles than you might first have thought, and we’ve got them right here.

The first step to knowing what hats will suit you is knowing your face shape, and this nifty tool from Philadelphia fine hat purveyors Goorin Bros is a good place to start, with tips for round, square, oblong and diamond-faced gents.

As well as all that though, figure out where your chosen hat will fit into your wardrobe and lifestyle. 

The perfect Panama, like our first choice hat from Borsalino, goes almost anywhere, making a great match for summer formal events, holidays and anywhere else you might conceivably have to board a fancy boat. 

For the perfect casual hat, baseball is where it’s at. Try the Loro Piana Storm System Baby Cashmere Baseball Cap for off-duty style with a bit of a luxurious twist.

A white Panama with a black band is about as traditional as it gets, so if you’re thinking of heading down South America way with your headwear, this is the route to take. 

Spectacular with summer suiting, or to elevate pretty much any casual outfit, this version from Borsalino is finished to perfection with a neat tight weave, grosgrain ribbon trim and a flourish of subtle branding. The internal browband keeps it comfortable for long wear, and the large brim doubles up as dapper sun protection.

If a traditional baseball cap has you feeling a little like an extra on a PGA tour, the wide, flat brim of a snapback might be just up your street, and they don’t come much more fashiony than an Alexander McQueen snapback. 

Forget the brightly coloured Fresh Prince options: this one keeps things thoroughly grown-up in all black, with just the right amount of detail courtesy of the contrast-stitched triangle logo. This is one that makes a statement, but keeps things well within the realms of respectability.

If you’re looking for a serious upgrade to the Yankees cap of your youth, you’ve found it. This Loro Piana baseball cap is made with outrageously smooth baby cashmere for a tactile detail that’ll top off any basic off-duty outfit nicely. 

But it’s not quite as high-maintenance as it sounds – the hat’s been coated with a patented Storm System treatment, so while there’s nothing to stop it blowing off your head in a force 9, it is waterproof and wind-resistant to keep your head toasty in winter weather.

We gave a shout-out to Goorin Bros in our intro, and with good reason: they really know their way around a hat. These trucker hats are among their most popular designs, thanks in part, we suspect, to their technically correct but undeniably cheeky embroidered patches, which range from depictions of beavers to roosters to (ahem) asses. 

If you’re a big fan of the breathable mesh back that makes trucker hats so comfy in the summertime, but still get uncontrollable flashbacks to the VonDutch days, consider these tongue-in-cheek hats as a high-end alternative.

Our best winter hat for men, and one that looks great on most face shapes, is the flat cap, but avoiding being mistaken for a cast member from Last of the Summer Wine is a fine art. 

Luckily, this cap from Lock & Co Hatters looks impossibly swish in its low-key navy tweed, and has an unmistakably high-end feel thanks to a premium wool and alpaca blend, fully lined with an internal satin browband. And for when the weather gets really frightful, there are cosy fleece ear flaps.

Fedoras can be especially tricky territory, but you’d have to try pretty hard to fall anywhere short of old-school glamour in this Brixton version, which takes all the guesswork out of looking dapper. 

This 100% wool fedora is worlds away from the oft-memed pinstriped version, with a flattering wide brim and narrow belt-style band, and the range of colours is great too, offering options to flatter all skin-tones from light tan to blueish grey to olive.

There are many types of beanie, from the Steve Zissou to the Jimbo Jones, but for us, nothing beats a Gucci beanie. This wool hat from the iconic Italian design house is aptly elegant and luxurious, superbly pared-back in its design, but soft to the touch and beautifully put together. 

The ribbed turn-up cuff not only keeps the pull-on hat where it should be – no uncomfortable slippage – it, plus the telltale grosgrain detailing, adds just the right amount of interest to an otherwise simple hat accessory. A great one for winter weekend dressing.

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