Oh My Hat!

What your choice in hat says about you


Words: Dylan Muhlenberg | Illustration: Sabrina Scott


The type of hat you choose to wear says a lot about you. Things like

“I’m a cop!”

“I’m a fireman!”

“I’m a cowboy!”

And in the case of those beer-dispensing hats:

“I’m a fun guy who can drink two beers at the same time while freeing up my hands to give passers-by the finger-pistols!”

For those people who don’t work a job that’s also a Lego figurine, a hat is the best way to finish off an outfit. It’s also something that will send out a message to the world quicker than your personality can. Fedora? You listen to psych rock and have some hand-poked tattoos under your fringed suede jacket. Feather in a fedora? You’re Jeremy Loops. Here’s our, not entirely scientific, take on what your hat says about you.

Cool if you’re fishing. Fine if you’re a rapper. However, if you’re adept at neither of these timeless pursuits then you’re just another poser who’s ruining this particular type of hat for rappers and fishermen.

Comfort: Like slipping into a warm bath.

Celebrity Endorsement: Earl Sweatshirt.

Practicality: The bucket hat provides protection for the ears, neck, nose, and eyes. In a pinch it can also be used to carry things.

Best worn with: Patterned button-up shirt, with the top button done.

Shade: Gazebo.

This hat has been seen everywhere and on everyone for about a year or two now, and is showing no signs of slowing down. Made up from five pieces of fabric, each cut specifically for where it will fit, the 5-panel is well-fitted and super-comfy.

Comfort: A glove, but for your head.

Celebrity Endorsement: Okmalumkoolkat.

Practicality: Ups your streetwear game considerably.

Best worn with: Swag.

Shade: A summertime essential.

The hat of the moment and those who know, know. Six is the devil’s number, and the devil is in the detail, which in this case is a six-panel design modeled off of retro baseball hats.

Comfort: Hot water bottle.

Celebrity Endorsement: Mat Kieser.

Practicality: A smarter version of the curved brim cap.

Best worn with: Sol-Sol, Carhartt and other workwear inspired brands.

Shade: Standing under the bleachers.

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The snapback is still ubiquitous. Don't worry about blending in though, as there's myriad ways of wearing these: over a do-rag, backwards, sideways, price tag attached, gold foil sticker…  Frat bros and mallrats attempted to kill the Snapback's vibe, but it’s shown grit by keeping its cool despite this.

Comfort: Jeans with sag.

Celebrity Endorsement: Jay Z.

Practicality: Can obscure red eyes when worn low and add height when needing to intimidate others.

Best worn with: Crisp white sneakers.

Shade: Subtweets and diss tracks.

You’re Irish, a street urchin selling newspapers dated 1920, a dude without the confidence to wear a fedora, bald, or Brad Pitt. 

Comfort: Jogger pants.

Celebrity Endorsement: Brad Pitt.

Practicality: A smarter hat option, which has the added benefit of keeping your head warm.

Best worn with: A waistcoat.

Shade: Umbrella.

If yours has “I (heart) Durban” running across the band and you’re wearing it on a Cape Town beach, great, wear it with pride. If not, you're not even on holiday and you’re not a scarecrow, then nah.

Comfort: Taking off your shoes at the end of a half marathon.

Celebrity Endorsement: Brad Pitt in warmer climes.

Practicality: It’s a lightweight option that’s great for the garden or the beach or holidaying where it’s hot.

Best worn with: In the case of the abovementioned scarecrow, dungarees. If you’re Brad Pitt visiting George Clooney’s Lake Como villa, a linen suit would do nicely.

Shade: Palm frond shack.

Tread carefully here. Either you get glad eye from the type of girl who wouldn’t usually give you a second glance, or you self-consciously carry around a head that you at least attempt to hold high as your mates crack Amish jokes. There’s a difference between the type of guy who gets glad eye and the guy who gets mocked: confidence. Channel your inner rock star and you're cool, otherwise you have no business wearing this hat.

Comfort: Bed of nails or bed of roses, it all depends on you.

Celebrity Endorsement: Harry Styles.

Practicality: Can make you look cooler than a polar bear’s toenails.

Best worn with: Stovepipes, brothel creepers, black.

Shade: Solar eclipse.

The hat loved by hipsters, skate rats and bald dudes. If it’s not winter then you shouldn’t be wearing one and if yours has those earflaps and it’s not snowing then you’d better be in a pop-punk band.  Like the Snapback there are many ways to wear a beanie and we’ll probably do a How To piece on this next winter.

Comfort: Tucked in by mommy for beddy-byes.

Celebrity Endorsement: Jacques Cousteau. 

Practicality: Keeps you warm. Hides your hair. Makes you look gangster. Doesn’t do much in the way of keeping the sun out of your eyes but you can’t win them all.

Best worn with: Outerwear.

Shade: Nah.

This all depends on what you have on the front of yours. A John Deere logo is cool. Witty statements like, “My other ride is your mom” aren’t.

Comfort: Sipping cans of lager while sitting on the stoep.

Celebrity Endorsement: Ashton Kutcher.

Practicality: Shade up front and breezy at the back.

Best worn with: Sleeveless flannel shirt.

Shade: Truckers tan.

This hat isn’t worn to stand out, it’s a form of camouflage used to try and blend in. The most casual of caps is not only the perfect hangover cap, it’s the best way to cover up greasy hair. Extra points if you’ve worn yours for years or it belonged to your dad.

Comfort: Induced coma.

Celebrity Endorsement: All the real ones.

Practicality: Deflects attention instead of bringing it – perfect, then for celebrities.

Best worn with: Aviator sunglasses and a pair of trailing body guards.

Shade: Security blanket fort.

If you’re still wearing a visor then you and your frosted tips are probably distraught at the fact that you can no longer purchase Safyr Bleu eyedrops over the counter anymore.

Comfort: Well-worn ¾ cargo shorts.

Celebrity Endorsement: Guy Fieri.

Practicality: Shade your face while sharing your frosted tips with the world. However if you have a thinning pate then you just get sunstroke.

Best worn with: Sunglasses on top of the head.

Shade: Standing behind a tall guy.