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Hide Your Uncut Hair: The Best Hats For Your Face Shape

Peaky Blinders Hats
(From left) Joe Cole, Cillian Murphy, and Paul Anderson in “Peaky Blinders.” Courtesy of Netflix

Depending on where you live, your favorite barber shop may well be closed for the pandemic since it’s not considered an essential business. Non-essential? Tell that to your hair that keeps growing further out of control while you’re stuck at home. You’re trying to keep a somewhat professional look for those video conference calls with the team from work, but what are you supposed to do in the Hairpocalypse? Turns out there’s a fix involving a cover-up: More and more men are turning to stylish hats to manage their manes and make a more professional presentation.

We talked to Kevin Todd Gerber, a veteran salesman at JJ Hat Center; a Fifth Avenue shop that’s been in business in New York City since 1911. Gerber, even though he has some long curls of his own, is himself lamenting. “It’s getting in my eyes! I mean I have long hair, but it doesn’t usually get in my eyes,” he tells The Manual. “Look at Conan O’Brien. He normally works that neat pompadour. Now he’s just kind of shaping the sides and slicking it back.” 

Gerber is one of many hat salespeople who have seen an uptick in hat wearers post-pandemic. “I’m not sure if it’s all for Zoom meetings, but hats are definitely helpful for covering up a weird mess of unkempt hair,” he says.

Beyond keeping your unkempt hair a bit more kempt, there are plenty of reasons to put a cap on: You can get them in almost any fabric, they’re lined with absorbent cotton or mesh linings (for sweaty heads), and they’re extremely portable.

And thanks to our current streaming obsession, bingeable Netflix series like Peaky Blinders, which follows a group of impeccably dressed 19th-century gangsters, have also contributed to the hat craze.

But he cautions against choosing hats that look like period costumes. “If you’re going to wear hats often, don’t choose something like a big cowboy hat,” Gerber says. “You can tell somebody is trying to cover something up, like baldness or something. It’s too much. Keeping it subtle is the real key.”

If you plan on wearing these hats during Zoom calls during office hours, make sure to make it a little ironic. Stay away from dark colors that are more evening-appropriate. Instead, opt for lighter, earthier colors that are more playful and laid-back. Unless you want to look like you’re trying to hike outside, stay away from bigger brims, which look flashier and showier. Try shorter brims that are two inches or less.

Ahead are some of the best hats to wear now, based on your face shape.

Best Hat for Men With Oval or Narrow Faces: Ivy Cap

For those unfamiliar with an Ivy cap, it features a wedge-shaped, narrow silhouette that’s understated, a far cry from your typical baseball caps.

“It doesn’t scream ‘Look at me,’ or come off as overly nostalgic. It’s great for guys with shorter hair and narrower faces. Slimmer styles are very hot now.” 

Our pick: Stetson Belfast Ivy Linen

JJ Hat Center Ivy Cap

This Ivy cap offers a summery, breathable linen version of the style. It’s available in a nice range of colors, but we like this black version for its simplicity.

Best Hat for Men With Wider or Rounder Faces: Newsboys

For guys with “big hair” or a bigger face, Gerber suggests going with a newsboy because it has more depth and width to accommodate bigger heads and unruly hair that you want to hide. Plus, they include little flops on the sides for a nostalgic edge.

Our Pick: Stetson Hatteras Newsboy Linen

Stetson Hatteras Newsboy Linen

Its cool linen naturally manages temperature, and also offers UVA and UVB protection.

Best Hat for Men With Square or Oblong Faces: Fedoras

Generally speaking, guys with thinner faces and high cheekbones are steered toward caps. Those with oblong faces — longer than wide, with a rounder chin — can be steered towards wider brim styles that sit low on the forehead to bring balance. But that doesn’t always look great on video conference calls, as wide-brim hats can cast a heavy shadow on your face, which can come off as a bit dramatic for an office meeting

Rather, stick with a medium-brim fedora. Its softer design work well with square faces — defined by a strong jawline, wide forehead, and wide cheekbones.

Our Pick: Bailey of Hollywood Billy Fedora

Bailey of Hollywood Billy Fedora

This short-brim fedora offers a bit more structure than regular fedoras, but its monochrome style keeps things simple, so it’s great for video; but still stylish for everyday.

Best Hat for Men With Heart-Shaped or Triangular Faces: Straw Short Brims

A teardrop brim hat’s low top is a great balance for men with protruding chins.

Our Pick: Goorin Laying Low Short Brim Hat

Goorin Laying Low Short Brim hat

Not only does this hat come in different sizes, but it is also packable, so it can take a certain amount of abuse as you move from conference calls to nature’s call once vacation time opens up.

Ultimately, the best advice is to find a headwear style that makes you feel good. “Get something in a color that flatters you and your eyes,” Gerber says. “Get a hat that you’re going to wear outside in the park, or on a date, or out on the town. Don’t just get one for bad hair days or for the pandemic.”

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