Girl in hat

Hats are a complicated accessory, part-costume, part-cultural signifier. In modern-day America, they’re mostly worn as a highly functional necessity: woolen skull caps to keep us warm, wide-brimmed straw versions to shade us from the sun or baseball caps to disguise bad hair. This isn’t England, where those cunning mini-hats known as fascinators are sometime formal requirements. Here, one false move and your headwear becomes a crime of pretentiousness (read: Williamsburg 20-somethings in top hats or L.A. blondes in wool fedoras despite 80-degree weather).

That doesn’t stop us from taking the leap sometimes: Two years ago, I optimistically purchased a wide-brimmed, chocolate-brown felt number fully intending to channel a breezy, bohemian French woman. But before I even wore it, my daughter spotted the thing perched on my bureau and laughed in my face. “You’re just not a ‘hat person,’ ” she said. But I wanted to be.

If ever I were going to try again, this would be my moment. Look around and more women than ever are pulling off that devil-may-care jeune fille look I had in mind. There’s a distinct movement afoot (or is it ahead?) that’s arguably gained steam since Saint Laurent creative director Hedi Slimane featured wide-brimmed hats on his spring 2013 runway to thunderous applause—a pivotal moment that not coincidentally kicked off the ’70s revival currently under way.

“Hats have taken over the scarf trend,” said Elyse Walker, owner of an eponymous Los Angeles boutique and fashion director of e-commerce site Forward by Elyse Walker. Ms. Walker said she saw hat sales last year increase around 150% at her Pacific Palisades boutique. E-commerce site Net-a-Porter, meanwhile, reported millinery sales nearly doubled. Marcus Wainwright, co-managing partner of New York-based label Rag & Bone said that the company can barely keep up with orders for its floppy-brimmed fedoras, constructed by heritage hat company Bollman.

That’s a lot of “hat people”—if you believe in such a designation. Los Angeles-based milliner Janessa Leone, 27, passionately rejects it. “That’s like saying you’re not a shoe person,” exclaimed Ms. Leone. “You have to wear shoes! There are so many different hats. You can find one that is flattering.”

Her advice is to keep it simple. “For me, [a hat] needs to be classic,” she said, “so you can’t tell if it came out of 2015 or the 1940s. It can’t be over-designed.” The original inspiration for most of her styles is a worn-in man’s fedora unearthed by chance at a vintage shop in Paris.

More than a few excellent brands make similarly timeless hats, including Rag & Bone, Eugenia Kim, newcomer Clyde and haute couture milliner Maison Michel. Saint Laurent also offers very fine, though pricey, versions to wear with its ’70s-inspired clothes for this season.

Whether a hat flatters you is, like everything else in fashion, a matter of proportion, said creative consultant, Cayli Cavaco Reck, who swears by hats, from a winter-appropriate Prada trapper to a gray cowboy style. Ms. Cavaco Reck particularly considers brim width. Wider is more feminine. “But not too wide,” she warned. “[For me], it’s not Jessica Simpson or J.Lo. It’s not for drama.” She added, “You can get it equally wrong with heel height or bags. But [those] aren’t at eye level, so you don’t notice as much.”

Net-a-Porter buying manager Sasha Sarokin suggested that beginners start off with smaller shapes, like the fedora, and stick to neutral colors. “I love the wool-felt styles from Maison Michel or Rag & Bone for a more casual look,” she said. “These are manageable in both size and color.”

But even with the right hat—one that’s classic enough, low-key enough and the exact right shape—you (OK, I) can still feel ridiculous venturing into public. So above all else, the trick to wearing a hat is swagger.

“You just have to go for it,” said Rag & Bone’s Mr. Wainwright. “Take no prisoners. If you own it, you look cool in it. You can look like you’re trying too hard quite quickly.”

Ms. Leone also stressed the need to make a commitment: “Don’t fidget with it or take it on and off. If you’re self-conscious, that’s the number one reason you won’t wear it well.”

It’s clearly a mental game. I suppose I should take comfort in the likelihood that, given how many hats have been sold, I won’t be the only “Girl in Hat” on the street when I take the plunge again—however conspicuous I might feel. As Ms. Cavaco Reck reminded me, historically a hat isn’t a means to look ridiculous, but rather polished. “It makes you look finished,” she said. “When Hedi Slimane put them down the runway, everyone thought, ‘Well, now that looks smart.’ ” Added Net-a-Porter’s Ms. Sarokin, promisingly, “It’s not uncommon to feel naked without your hat once you’ve gotten used to it.”

What About My Hair?

It’s important to nurture a good hat-to-hair relationship, a la Leslie Caron in this straw number in 1965.
“THE HAT will tell you what you need to do with the hair,” said Wes Sharpton, a stylist at New York’s Hairstory Studio, somewhat cryptically. Translation: Before you buy a particular hat, take a clear-eyed look at how it works with your particular hair. “Even if [the hat] is amazing on its own, on you it might be a disaster,” he said.

However, a quick hair makeover can sometimes rescue an ill-conceived purchase. “[It’s] something nice and sleek so your jawline is showing,” she said. Something softer like a fedora is flattering with loose locks. If you’re leaving your hair down and long, she advises playing up your natural texture with a sea-salt spray, like one from La Tierra Sagrada. Another option: a loose, centered braid—with the sides tucked behind the ears and pulled tight—that you’ve added some grit to with Oribe’s Dry Texturizing Spray before it is plaited. It’s a bit bohemian but also sophisticated.

As for combating that dreaded post-hat flatness, Mr. Sharpton suggested a simple and product-free trick. Before you put on your hat, flip your hair in the opposite direction of the way you usually wear it. “Then you just flip it back when you take your hat off. That’s what builds lift.”

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