How To Wear a Hat Without Looking Like a Fool

When it comes to relationships, finding the perfect match could be as simple as swiping right. But as far as hats are concerned, The One 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 trilby.

With such a barrage of 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 etymological roots lie in the Greek word for ‘gift from God’, and it’s a style that’s fallen in and out of favour since the late 19th century. In prohibition-era America, for example, it became synonymous with gangsters, which is pretty rad, 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 Stetson and pork pie.

Who Wears It?

History is full of examples of men who harnessed the rakish flair of the fedora. Indeed, 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. And, in the case of James Bay, savvy record execs have even used a fedora to trick us into thinking his dreary, middle-of-the-road music is actually moody, interesting and worthy of merit. Impressive stuff.

(Related: The best dressed men of 2015)

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.

The fedora’s tall, dented crown means it suits shorter guys or those with a bigger build, as it adds height, draws the eye upwards and elongates the frame. As for the brim, consider your face shape before committing to a slim- or wide-brimmed style: a longer, oval-shaped face benefits from the proportion-balancing effect of a wider brim, while a slimmer brim will streamline a rounder, squatter face. And if you’re blessed with a chiselled jaw, well, my friend, yours is a world brimming (yup) with options.

“In short, a hat like this won’t work with jeans, trainers and a sweatshirt,” says Matt Hambly, Associate Style Editor at Men’s Health. “Secondly, 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 crew neck T-shirt tucked into tailored trousers worn with a pair of Derbies, or steer traditional with checked tailoring and some expertly manicured facial hair.

Current Styles

• BRIXTON WESLEY FEDORA
• ASOS FEDORA HAT IN CAMEL FELT
• ZARA FELT HAT
• M&S COLLECTION PURE WOOL FEDORA HAT WITH STORMWEAR
• TOPMAN FEDORA HAT
• HE BY MANGO WOOL FEDORA HAT
• RIVER ISLAND BROWN FLORAL TRIM FEDORA HAT
• RRL RABBIT-FELT FEDORA
• ALLSAINTS BRONSON LEATHER FEDORA HAT

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

Who Wears It?

The humble baseball cap might be camouflage for celebs seeking to go incognito (Beckham defaults to his 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?

With pretty much anything. Even a suit. Well, not all suits (Trump, stay woke), but arguably the most on-trend way to work a baseball cap into your rotation is with crisp, clean and monochrome tailoring.

Designs constructed from suede, leather and wool have put a luxe spin on this sports staple, making it ideal for styling with deconstructed blazers and sports jackets.

Just make sure yours is facing forward. And doesn’t promise to ‘Make America Great Again’.

Current Styles

• EBBETS FIELD FLANNELS STANDARD ADJUSTABLE CAP
• STUSSY STOCK TONAL WOOL CAP
• A.P.C. CLASSIC CAP
• NEW ERA 9FORTY SCRIPT ADJUSTABLE CAP IN FAUX SUEDE
• JACK WILLS CALENDON WOOL CAP
• TOPMAN STONE AND GREY SNAPBACK CAP
• TED BAKER TINGHAT WOVEN BASEBALL CAP
• AMI STRETCH-COTTON BASEBALL CAP
• BALMAIN LEATHER AND COTTON BASEBALL CAP

The Beanie

What Is It?

Essentially a knitted cap, the beanie has – in some way, shape or form – been around since the 1100s. 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 have pom-poms. Don’t wear those.

(Related: The pieces no man should have in his winter wardrobe)

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 the suave Daniel Craig to every guy’s bearded man-crush, Jake Gyllenhaal.

The fact that brands like 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 is an outright no-go – i.e. when it sits sloppily on the back of your head covering a head full of hair/secrets.

“Balance a beanie’s casual leanings with structure,” says Luke Raymond, ASOS Menswear’s Fashion Editor. “Small, rolled up helix 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.

Current Styles

• THE ELDER STATESMAN BUNNY ECHO CASHMERE BEANIE
• J.CREW MELANGE KNITTED BEANIE
• BEAMS PLUS LINEN WATCH CAP
• HE BY MANGO RIBBED BEANIE
• RIVER ISLAND BROWN RIBBED KNITTED BEANIE HAT
• ZARA COTTON KNIT CAP
• RECLAIMED VINTAGE MINI FISHERMAN BEANIE IN BLACK
• ASOS FISHERMAN BEANIE HAT IN GREY
• ASOS FISHERMAN BEANIE IN BURGUNDY LAMBSWOOL

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 1990s, it became the headgear of choice for wayward boyband members with addiction issues and old timers whose sartorial prowess just wasn’t ‘what it used to be’.

In 2016, however, all’s 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, providing a sartorial alternative to the sporty baseball cap.

(Related: 10 of the best men’s hat brands)

Who Wears It?

Unsurprisingly, this is a style still favoured by the likes of Prince Charles and East Anglian octogenarians. But it has its stylish flag-flyers, too – among them David Beckham, Idris Elba, Oliver Cheshire 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.