What Your Cap Says About You

The meteorologists are predicting a bitterly cold next few months, which means the winter hat isn’t just a fashion accessory – it’s a necessity. Still, going out in the cold doesn’t require a sacrifice in style and personality. Here is a guide to men’s hats and what they say about those who wear them.

Cossack Hat

For: Aspiring Siberians, fur lovers and the wimpiest of winter survivors.

Luxury label D&G was pushing the Russian fur hats at their recent Fall/Winter show but we remain unconvinced. High fashion may be encouraging the Gogol-era raccoon-on-the-head (Nikolai Gogol, 1809-1852) look but unless you’re a miserable bureaucrat who has to live through a -40C winter in St. Petersburg, there’s less reason for you to wear one of these. In any other climate, this hat can make you look like a sissy who is overprepared for a cold-blast that will never come.

Hockey toque with pom-pom

For: Bob and Doug Mackenzie and anybody who can recite the I-am-Canada monologue.

There’s something childishly fun about these hats that harken to the days when the outdoor rink was the place where one learned how to skate. The NHL knew this too: The 2003 Heritage Classic game that featured the Edmonton Oilers and the Montreal Canadiens in -35C weather brought these hats back from the vintage stores to the accessory-du-jour for hockey fans. (Players wore the neo-retro hats on top of their helmets for the game). But as the Mackenzie brothers proved, few things are more Canuck-like than this toque, so remember: Wearing it may turn you into a Molson-swilling hoser.

Headphone beanie

For: The ironistas with the printed tees and skinny black jeans; those who can’t figure out how to wear a hat over earphones.

A winter hat with built-in earphones in the ear-flaps? Ever since the Walkman was invented, kids have figured out how to listen to their favorite tunes while walking to school without the help of special hats but finally winter-wear company Burton has made it easy for the next generation. Included is a special set of removable headphones that are complete with cord-mounted volume and mute controls. The beanie design is oh-so-au-courant – expect this one to be a hit among the freshmen set.

Newsboy hat

For: Cliff Huxtable wannabes and anyone who wants to hawk papers on a street corner.

It’s a classic that has survived for good reason: It looks good on young and old and has a bit of brim to protect from the sun. It reminds us of times when kids shouted “Extra!” and when there was such a thing as an evening paper. However, in our colder climes, ears remain unprotected, so with the exception of those who live on the West Coast, the Newsboy hat is still a luxurious second hat in our winter wardrobe – but recommended nonetheless.

Hunting hat

For: Appreciators of good hat design despite comparisons to a hapless cartoon character.

Oh, Elmer Fudd: How you’ve stolen this hat and forever taken it to the Land of Ridicule. It’s unfortunate because it’s actually one of the most practical and least ostentatious hats out there: A full brim to block the sun and easy ear flaps that aren’t over-the-top (see Cossack Hat), the classic hunting hat should be a best-seller. Unfortunately, anybody who wears it will endure an endless barrage of “Wabbit” jokes. And though we love the practicality of the design, we admit, we’re not above the lowly one-liners either.


For: Xtreme winter sport athletes and paramilitary recruits.

If the intent is to scare bank tellers, wear one the next time you make a deposit. Still, for anybody who prefers skiing in the frigid cold – way fewer posers on the hill when it’s -35C – or is thinking of joining an extremist organization, this accessory is an old standby. If you have to get one, go full tilt: This Mountain Equipment Co-op number is made of thermal fleece and provides maximum coverage and a stiffened visor to make sure no amount of frost will block your vision.