How to Choose a Hat That Doesn’t Make You Look Like an Idiot

Texas hat experts share their tips on how to select a lid that won’t make you look like an idiot.

For a long time, choosing a hat was easy for me: I simply didn’t. I saw The Hat as a fashion flex (way before I knew that term), an eccentricity that involved image management and risk. Of course, I’d known hat people, stylish types who could pull off a fedora or a bowler, but I’d also encountered try-hards who were practically wearing a sign asking “Am I cool yet?” Raffia Straw Sun Hat

How to Choose a Hat That Doesn’t Make You Look Like an Idiot

I’ve come to realize, though, that head coverings are useful, which must be why our ancestors invented them. They are handy in sun, rain, and bitter wind, to say nothing of how well they disguise bedhead and bald spots. Over the past decade, they’ve made their way into my closet in ever-increasing degrees of boldness: baseball caps became beanies became sun hats became a steel-gray Stetson. More recently lids have surged in the culture, too, thanks to the soapy stylings of Taylor Sheridan’s Yellowstone, musicians across multiple genres, and probably some Kardashian.

The trend hit satire level earlier this season on Saturday Night Live, which brought us a fake commercial for Big Dumb Hat, a send-up of women who flop their way across Starbucks and Sephora. The bit, starring host Amy Schumer and two female cast members—all sporting mermaid hair, neutral tones, and large lids (Schumer’s grew bigger as the skit progressed)—was less about hats and more about trend-chasers prone to look-at-me gestures. “Do you want a personality that you can wear on your head? Then you need Big Dumb Hat.” 

“I loved that sketch,” says Brittany Cobb, the owner of Flea Style, a clothing and accessories boutique with three locations in Dallas–Fort Worth, including in Frisco at the Star District, the shopping complex attached to the Dallas Cowboys’ headquarters. When I met up with her there, she was wearing a toffee-colored Stetson atop her wavy blond hair, but unlike one of the women in the SNL skit, she was not drinking a tiny cup of oat milk from Starbucks. (It was a peppermint mocha.) Cobb dons toppers so often that during college two decades ago at Southern Methodist University, she was sometimes called “the Hat Girl.” 

Every Flea Style features a hat bar full of options for customizing your topper, which you can do with the help of a stylist. For $20, you can reserve an appointment, complete with a flute of champagne. (Or you can just walk in and buy the headgear of your choice off the rack.) The store hosts hat parties for as many as fifteen people, along with larger corporate events; on the day I visited, Cobb mentioned a recent such fete she’d thrown for the executive team of a railroad owned by investment magnate Warren Buffett. Flea Style’s interior decor is quite feminine, a lot of pink and boho chic, but roughly a quarter of its hat customers are men. 

Cobb grew up in Southern California, the daughter of an interior designer who let her tag along to antique malls and flea markets, a habit she continued in college at places such as First Monday Trade Days, a popular monthly market in Canton, about an hour east of Dallas. Eventually she began doing her own pop-ups featuring vintage finds. Cobb launched Flea Style as an online venture in 2015 and opened her first brick-and-mortar boutique, in Deep Ellum, in 2018. Hats are about 50 percent of her business, including accessories to personalize them, such as vintage brooches, rhinestones, feathers, and cool retro matchbooks. 

Customization bars such as Flea Style’s have taken off across the state. When I told a friend about this trend of decorating hats with various baubles, he cracked, “Wait, I thought this story was about how not to look like an idiot.” Sure, a vintage brooch pinned onto a Stetson might not be everyone’s idea of a chic look, but maybe the first rule of wearing a hat is knowing that one person’s style is another person’s folly, that fashion is subjective, that expressing your personality through clothes brings the threat of scorn but also the promise of feeling understood. 

My friend doesn’t wear hats. “My head is too big or something,” he told me. In other words, he doesn’t know how to wear a hat without feeling ridiculous. I’ll let Cobb, and a few other experts from across the state, help out.

“A really wide brim on a smaller face can look overwhelming, kind of costumey,” says Cobb. She happens to have “a big ole head,” so she wears three-and-a-half-to-four-inch brims, but the smaller noggins among us might prefer three-inch brims or fedoras. Same goes for the hat’s crown: a shorter person might like a lower crown, to remain proportional. Though Flea Style has many choices, Cobb sells her own style of hats (the Brittany), made by Stetson, for which she chose a flat brim, unlike the classic Texas brim, which is curled like a hard taco shell. 

The anthropology of hats is a story of its own, but back in the day, an expert could identify a cowboy’s hometown from the brim and crown of his Stetson, the way you can place an accent. Many in South Texas go for a wider five-inch brim (closer to the original sombrero), while some in northern states like Wyoming wear a rugged flat crown and straight brim, known as the buckaroo look. These days, those distinctions matter less than comfort and personal preference. Cobb wears her hat far back on her head, much like iconic movie cowgirl Dale Evans, creating a halo effect designed more for looking good than riding herd. Evans always had to be camera-ready, but then again, in the age of social media, don’t we all?

“People buy online and order way too big,” says Devin Marcum, the national sales manager for the Western division of Hatco Inc., whose 85-year-old factory in Garland  makes about 4,500 hats a day, including many Stetsons and Resistols. He’s seated in an office with framed portraits of his family as well as Roy Rogers (Evans’s husband and costar), and he’s wearing a black fleece vest, a button-down shirt, and a black cowboy hat, a Resistol 40X Arena. The standard hat size for men and women is seven to seven-and-three-eighths, but Marcum says too many shoppers order size seven-and-a-half lids. “Do they assume their shoe size is their head size?” he wonders. Hats have a specific calibration, with sizes that scale up in one-eighth-inch increments. (The best way to determine your size is to try several on until you find a fit that’s snug but not too tight, but you can also measure at home using guidelines on a retailer’s website.) Women’s sizing also depends on how big their hair is. And this is Texas, so ladies, leave a little room.

Most hats are black or shades of brown, silver, and white. But at Goorin Bros., a San Francisco–based chain with locations in Dallas’s Deep Ellum and on South Congress, in Austin, options get flashier. “We push the envelope on color,” says Dallas manager NaChole Jackson, wearing a cranberry fedora with feathers atop her long bronze and magenta braids; her nickname is “the Fab Hatter.” We’re standing in a store filled with fedoras and trucker caps (the store’s specialty) in canary yellow and cobalt blue and even tie-dye alongside more neutral tones. 

“Find yourself in the hat,” Jackson tells me, plucking a navy suede pageboy (a newsboy-style cap) off the shelf so I can try it on. 

“Aren’t these for men?” I ask, tugging on the cap, but Jackson explains that, like those of most brands, their hats are unisex. She adjusts my pageboy to a jaunty angle and stands back to let me see the mirror. 

“Oh my God, I feel like a pop star!” I exclaim—I was thinking Beyoncé, bless my heart—and she just smiles.

“People just put on a hat,” Jackson says while shaking her head, “and if it doesn’t look right, they’re like ‘Eh, not for me.’ ” What they don’t realize is that donning a hat requires finesse. Jackson demonstrates with a fedora called Dean the Butcher. She slides her manicured fingers alongside the creases in the crown that are basically handles. “Line the front seam along the center of your forehead,” she says, tipping the hat back in her hand like a dancer whose routine is about to start, A Chorus Line–style. “Then let it fall back onto your head, and adjust it using the sides.” 

I made her do this three times, knowing I could never be so smooth. 

Most hat rules have gone the way of the wagon wheel. People wear them inside these days, and few feel the need to take them off for ladies, especially if you are one. But anyone wearing a hat should remain aware of the environment. Maybe remove it for dinner or in churches or movie theaters, anywhere you might block someone’s view—unless that view happens to be a concert by Jason Aldean, Madonna, Kacey Musgraves, George Strait, or any number of hat-loving artists—in which case, party on. 

“I wore hats for about half my life before I realized they were made of rabbits and beavers,” says hatter Cheyanne Summer Hatley. (Yes, that’s her real name.) She works at Herb’s Hat Shop in San Antonio. (It also has a location in Blanco.) I confess I had no clue that some high-quality hat felt was made from various animal furs, a fascinating process that explains the range in cost and durability. Beaver fur is water-resistant, while mink and chinchilla offer a silkier texture but a higher price tag. “Have you heard of nutria?” Hatley asks, and I shudder. Those big aquatic rodents are the stuff of nightmares, but their fur, which insulates them in cold water, can get thrown into the mix. Which brings me to another key point: you can also buy vegan hats. 

The mistake Hatley sees most is the impulse buy, someone grabbing a random hat on a whim. Those purchases often wind up in the back of the closet, an expensive regret. “A good hatter is as important as a good barber or nail tech,” she says. 

One of my friends once told me, “I’m not gonna wear a cowboy hat if I’m not a cowboy.” Fair enough, but he was wearing a flannel shirt, even though he isn’t a Welsh textile worker, and combat boots, though he’s never seen war. At what point does a uniform tip into a trend where everyone can play?

“LBJ wore a cowboy hat, and he was the president,” Hatley reminds me. His brand was a silver Stetson Open Road, a two-and-three- quarter-inch brim, more cattleman’s hat than manual laborer, and a reminder there’s a hat for everyone. (Even Elon Musk.) 

Hatley can’t stand it when folks who have their hearts set on a hat let friends talk them out of it or lose their nerve thanks to old stubborn fear. Looking foolish is a common anxiety among the hat abstainers. The wrong hat is uncool, everyone knows, but real cool is only ever achieved by people who don’t worry so much.

This article originally appeared in the March 2023 issue of Texas Monthly with the headline “Don’t Let the Hat Wear You.” Subscribe today.

Emily McCullar is a senior editor covering pop culture, news, and Texas history. One time she wrote about sports.

Forrest Wilder writes about politics and the outdoors.

Mimi Swartz is a staff writer based in Houston.

Katy Vine has been a staff writer since 2002.

Skip Hollandsworth specializes in long-form narratives.

How to Choose a Hat That Doesn’t Make You Look Like an Idiot

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