How To Wear Hats For Guys

No hat, no play.

How To Wear Hats For Guys

The hat is a much-maligned piece of clothing these days. It seems like someone is always complaining or making snarky remarks about the gentleman’s chapeau, but it’s only because they fear what they do not understand. Namely, how to wear a hat.

Not only is a hat a suave way to finish off an outfit, it’s also a versatile, functional men’s accessory that’s appropriate in any season. Sun, snow, rain, sleet…there’s almost nothing Mother Nature can throw at you that won’t be assuaged by the addition of a hat.

Brush up on the different kinds available, then surf through our gallery of headgear inspiration and ideas. You’ll soon see the hat is an effortless and inspired final touch.

Hat styles get as creative as the people who wear them, but these are the basics you need to know to stay shady and cool.

Panama Hat

Ecuadorian in origin, the Panama hat is traditionally made from the plaited leaves of a palm-like plant. Light in colour, the Panama is associated with seaside and tropical locales (along with historic heavyweights like Teddy Roosevelt and Humphrey Bogart).

A bespoke Panama hat called a Montecristis, made by specialist Ecuadorian weavers, can have more than 1600 weaves per square inch and is graded under rigorous conditions by a foundation from the Panama hat’s town of origin.  On the #menswear landscape, the Panama reigns supreme. Nearly every aspiring peacock at Pitti Uomo is decked out in one during the June edition of the show. Due to its superior ventilation and modest weight, the Panama is an ideal accompaniment to a summer suit.

Do consider a Montecristis as an investment piece if you want to do summer in style – they’re made by local manufacturers and are becoming a rare breed due to global competition and high prices.

Don’t wear it out of season – it’s designed for blue skies and can look discordant with darker autumnal or winter tones.

Fedora Hat

The fedora seems to be caught in a bit of a love-hate pattern with the sartorially-conscious public. Sure, Fred Astaire wore one, but so does that creepy guy that plays World of Warcraft and doesn’t wear deodorant. They were once worn by businessmen worldwide, yet now it’s hard to shake the impression that they’ve been swallowed by less stylish denizens of society.

However, the fedora is being steadily reclaimed by creative sartorialists who appreciate its accessible nature across the casual-formal spectrum. A fedora has a lengthwise crease down the crown, and the ‘pinch’ on either side of the front. A well-made number should be made from felt, with a firm (but pliable) brim. They’re made in varying widths and colours, but you’re best off sticking to neutral tones and a mid-size width. The fedora trend seems to have peaked, but they’re still floating about in various guises and there’s no reason not to catch on and give your clay and comb a break.

Do invest in a ‘proper’ fedora. High quality felt hats retain their shape and colour over time, compared to discount department store variants. Specialist hat brands – like Akubra – have expertise and don’t dilute their focus with other ranges, and its such companies that deserve your attention (and dollars).

Don’t wear the brim down with casualwear. Pop it up, so you don’t look like the kind of guy who read The Game and took it seriously.

Bowler Hat

Originally designed for the notoriously-fastidious British aristocrat and parliamentarian Edward Coke, the esteemed bowler hat is about as British as awkward small talk and ghastly weather. Despite its posh origins, it became a popular working-class accessory before being wrestled away by upper-class chaps who worked on London’s City banking circuit.

It’s unique appeal also led to an explosion of popularity among indigenous Bolivians women and of course, the rugged, lone gunslingers in America’s Old West (it was in fact more popular than the archetypal cowboy hat). Whether it’ll make a last stand in today’s #OOTD roster is anyone’s guess, but if the fedora can come back with a vengeance then why not the bowler?

Do commit to the look if you can’t resist wearing one. Double-breasted suit, umbrella, vintage Jaguar, posh accent – the works.

Don’t expect your mates to let you down easily if you wear one.

Dad Hat

No one grows up aspiring to look like their dad (unless he’s George Clooney). Against all odds, the dad hat has smashed this cultural standard to pieces and 2017 looks like the year where older men are once again sartorial heavyweights.

The dad hat is essentially a baseball cap with an ageist title. Middle aged suburban dads love the sh*t out of them – they’re comfortable, cheap, and an excellent alternative to hair regrowth treatments – and this embracing attitude has filtered through popular culture, until it ended up in the arms of millennials and other cool kids.

Do take the opportunity to find one with a wry wink at pop culture. Various brands put logos and slang that cleverly reflect the zeitgeist in some way. If that’s your jam, the contemporary dad hat is a fertile playground.

Don’t forget that this is a casual staple – keep this limited to tee-jean-jacket combos. You’ll look like a baseball coach at a press conference if you wear it with tailoring.

Snapback Hat

The snapback shares a few traits with its cousin, but it can be distinguished by its firm flat brim and adjustable back. It’s less forgiving if you have an oddly shaped head, but it’s become irrevocably associated with American streetwear and its global offshoots.

However, the snapback seems to have taken the backseat to the dad hat over the past year. Despite the new competition, the snapback still resonates in urban music circles and is hugely successful in sportswear.

Don’t wear it outside with the sticker on the brim.

Do follow the previous rule at all times.

Trilby Hat

The Fedora-Lite, the trilby is distinguished from its more prominent cousin by a shorter, low-angled brim. Although it enjoyed a golden age of respectability in the 20th century, it’s no longer a common feature in the corporate wardrobe.

Today, the trilby is commonly associated with gamers and pickup artists, undermining its previous esteem and connection to the working man.  In recent times, Bruno Mars has given it his best shot to pluck it away from an ignominious sartorial end, so announcing its permanent demise might be premature.

Newsboy Cap

The newsboy hat was a smash hit among working class Britons in the 20th century. Dockworkers and tradesmen favoured this hat, among others. It’s characterised by a curved brim, puffy eight panel body and top button. Considered old-fashioned for a time, the newsboy hat has resurfaced. It’s adaptable and adds character to a plain casual ensemble – think a white tee, Timberlands, and jeans.

Do invest in a Harris Tweed cap. Harris Tweed is indestructible and an absolute lifesaver in winter. You’ll also be supporting venerable English fabric mills that are the last of their kind.

Don’t get one with an exaggerated body – it can make your head resemble a woollen balloon.

Flat Cap

The flat cap is another working-class hero, and a close relative of the newsboy. It differs from the newsboy by eschewing the top button and puffed shape. Although its popularity peaked in the early 20th century, it has enjoyed a resurgence for its vintage appeal, ease of wear, and its simplicity as an addition to a weekend ensemble. It’s best suited to a nippy weekend drive to the hills or lazy brunches.

Do use it as a sturdy alternative to a beanie in autumn. While it’s not as warm as a beanie, a wool-cotton flat cap is a touch dressier and has far more character.

Don’t get one in leather – it’ll make you look like an Irish mobster and leather hats aren’t hugely comfortable as it is.

Boater Hat

The boater hat is a formal summer hat that peaked in popularity in the late 19th and early 20th century. The boater hat is made of stiff sennit straw with a grosgrain ribbon around the crown.

This style of headwear is a sartorial unicorn in today’s menswear landscape, and seldom worn outside barbershop quartets, period dramas, and posh school uniforms. As it’s a formal piece, it’s usually worn with a lounge suit or its closest summer approximation.

The boater hat is a definite statement and not for the understated dresser. But if you’ve always wanted to start a barbershop quartet, you can at least tell yourself how damn sharp you’ll look while busting out some tunes with your pals.


The beanie has undergone a long transformation from being utilitarian cold weather kit to a high-street accessory.  Luxury heavyweights haven’t shied away from featuring beanies in recent collections, giving them a wider audience outside streetwear circles.

On the #menswear circuit, it has become common for the debonair gent to combine traditional tailoring pieces – suits, blazers, overcoats – with beanies as a final winter accessory. Never thought you’d see the day? It goes to show that the beanie has versatility outside streetwear. There’s a ton of options out there: chunky woollen turnback numbers, ribbed two tone options, and monochrome cotton fisherman beanies.

Do be a grownup and get a fitted beanie. The sagging, drooping-at-the-back thing looks like a poorly fitted condom and has no place in 2017.

Don’t be afraid to combine a (properly fitted) beanie with your tailoring. A winter suit, trench coat, and sleek navy cotton beanie combines rugged masculinity with sleek tailoring perfectly.

Pork Pie

The Porkpie hat is another relative of the fedora. It’s small and round, with a flat crown and a crease along the inside top edge. Its narrow brim and shrunken shape led to its comparison to a pork pie – hence the name. The porkpie, incidentally, was originally favoured across the Atlantic by women before being co-opted by an enthusiastic male audience in the 20th century.

The porkpie’s recent notoriety can be attributed to Breaking Bad, where it became a recurring accessory for Walter White in his menacing Heisenberg persona. It’s also popular among the law-abiding public as a casual addition to a weekend outfit, where a fedora might be too demonstrative and a beanie might be too street.

Do get a porkpie in felt over other materials – it’s more versatile, in both season and style, than straw porkpies.

Don’t give yourself an alter ego whenever you wear one (Breaking Bad didn’t end well for Walter White, remember).

Bucket Hats

Bucket hats have managed to crawl their way out of the ashes of the 90’s, and onto mixtapes and dancefloors worldwide. The bucket hat derives its name (surprise surprise) from looking like an inverted bucket with slightly flared edges.

Bucket hats are a big hit in various electronic music subcultures, but the vote is still out on whether they’ve earned a seat at the table. But they’ve been doing the rounds for a couple years now with no sign of slowing down.

Don’t wear one if you take yourself too seriously.

Do unleash your inner 90’s hip hop fiend and wear it on your next night out with the boys. You’ll look back on it in five years and laugh (and be laughed at, probably).

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