In the dog days of summer, getting dressed means walking a fine line between style and comfort. Err too far on one side and you’ll risk spending the day marinating in your own perspiration; lean too much in the other direction, however, and you could come off looking, well, too comfortable. Further complicating matters, if your day includes spending more than a few minutes outside wearing a hat is a matter of necessity. Breezier than your standard ball cap or bucket hat, with a brim that’s as broad and shady as a Southern veranda, the straw hat seems like the perfect solution. Unfortunately, whether you’re dressing for a summer wedding or a day at the beach, straw hats also have the annoying tendency to make you look like an extra in Oklahoma! or a member of a barbershop quartet. The good news? With the right piece and a little finesse, it’s absolutely possible to integrate a straw hat into your summer wardrobe.
There’s a surprisingly wide variety of straw styles to choose from, including jaunty boaters and beachy lifeguard hats, but for most folks, the selection will come down to two basic types: the western or the Panama. The former, thanks to its longstanding association with cowboys, farmers, and country music festivals, has a distinctly more casual, workwear-adjacent vibe, making it a lighter lift than the dressier Panama.
Courtesy of Crust Young
“If you’re new to wearing cowboy hats, getting a hat with a smaller, less dramatic brim can make it more digestible,” advises Crust Young, a.k.a. Cowboy Crust, an LA-based content creator and western wear aficionado. “The Stetson Open Road is probably the best hat to dip your toe into the western world; it’s a classic, understated look that you can wear with almost anything.” From there, he says, you can graduate to more advanced styles like the Regal and the Primo Cognac, whose larger dimensions give them a more typical cowboy silhouette.
As a supporting character in the extended workwear universe, it follows that the straw cowboy hat looks best when worn alongside similarly hard-wearing pieces like work shirts, white tees, and denim. “While we don’t make straw hats, we are strong proponents of them,” affirms Andrew Duro, director of retail operations at Wythe, a brand whose catalog of vintage workwear-inspired designs seems specifically made to complement the straw cowboy hat’s crisp lines. “A straw hat only works if it feels a little wrong,” he adds. “Either a little too big, too unstructured, or too tilted to one side. They’ve always been for people too busy to care what they look like, which is of course what makes them look good.”
Courtesy of The Anthology
The Panama, by contrast, is a fedora-style hat traditionally woven in Ecuador from the leaves of the toquilla palm, and strongly associated with linen suits, tropical locales, and the type of guy who stays at the White Lotus. Fedoras are a big swing at the best of times, but according to Buzz Tang, the cofounder of Hong Kong-based tailor The Anthology, looking good in a Panama is simply a matter of not overdoing it.
“Think relaxed elegance, not retro formality,” says Tang, who suggests wearing a Panama with an unstructured sport jacket, a linen shirt, and a pair of lightweight trousers, or (for a more vacation-y vibe) a guayabera or a towel-cloth polo. The other key component, he adds, is the setting. “I think wearing it at the right time, right place is crucial,” says Tang. “Think Sifnos, Mallorca, or the Maldives—resort settings where a straw hat feels natural, not just nostalgic.” It’s sage advice. Whatever type of straw hat you choose, context is the secret ingredient to making it look right.
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