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Hats are the unofficial mayor of fashion’s uncanny valley. By all outward appearances, they’re exactly like clothes; like a shirt or pants, hats cover up part of your body, they come in a variety of sizes, and they’re soft. But for all their vague familiarity, vast swaths of the stylish masses feel somewhere between ill-at-ease and completely repelled by the idea of incorporating a hat into their everyday outfits.
In truth, the reason people are put off by hats is because they’re not used to what they look like in one, much like you might dislike how you look in glasses or a new haircut the first time you glance in the mirror. "As it goes with all new experiences, wearing a hat takes some getting used to," say Ben Goorin, president of Goorin Bros. Hats and fifth-generation hat maker.
But you don’t have to have Gisele Bundchen’s bone structure or a complicated haircut to become the Hat Person you’ve always wanted to be — you just have to put one on your head. With August’s hottest days still ahead of us, it’s time to try out some stylish sun protection — especially now that so many summer hats can be found on sale.
Check out our breakdown of the most wearable styles below.
If you only have one hat in your closet right now, chances are it’s a baseball cap. Why wouldn’t it be? They’re simple, they’re casual, and they’re low commitment. You can get one in any color humanly conceivable, and if you decide you hate it, you can always give it to your dad. This is the Levi’s 501 of hats.
"There is a baseball cap for everyone," agrees Goorin. "There’s only one wrong way to wear a baseball cap, and that’s not to." Basic styles with only slightly curved brims are most on-trend right now (thanks, normcore); you can find them in every price range, from the $5 caps at your local dollar store to the fashion-y hats (from $25) that Goorin makes to super well-constructed versions from brands like A.P.C. ($79).
Though these hats have been around since at least the 1890s, they’ve been popping up on more and more stylish heads lately. If you like the look, opt for a straw version with a solid band for an of-the-moment take. "Boater hats should have a short crown and a proportional brim to ensure that the shape stays current and fashion-foward," says official milliner of cool girls, Eugenia Kim, who makes the white ribbon version ($213) pictured above. If you want something less splurge-y, opt for the BP bow band boater ($12) available at Nordstrom. Either way, look for a one with an elastic band attached at the sweatband so you can be sure it won’t go flying when the wind picks up or you take off running after the ice cream truck.
If Elizabeth Taylor and Esther Williams are among your style idols, you might want to try out a turban this summer. Though they don’t provide much shade, you can protect your hair while you lounge poolside and keep your neck from getting damp with these babies. Best of all, you can throw most contemporary turbans in the wash should you sweat through them. You’re probably not going to want do that with the silk Valentino turban ($400) pictured above, but it would be a pretty safe bet with this Amazon find ($5), which is a great option if you want to test out the look before trading up to something pricier.
A wide-brimmed, floppy sun hat can run the gamut from something you crush at the bottom of your beach bag to the last word in fancy haberdashery. They’re versatile, provide a ton of shade, and you can find one that works for you regardless of your price point. Look for one that rests right above your ear and fits closely (but not tightly!) so you can relax on the beach rather than straining to see your magazine from under the brim. San Diego Hat Company makes a number of easy, inexpensive hats in this style, including their best-selling ribbon braid hat ($38); look to just about every other brand mentioned in this post for even more options, like a fancy color-blocked number from Eugenia Kim ($340), the hand-woven Davida Lynn hat from Goorin Bros ($102), and the sunny crocheted hat shown above by Mar y Sol ($60).
Ah, the bolero. Traditionally the domain of gaucho and Zorro, the bolero entered the modern fashion lexicon when Beyonce wore one in her Formation video. Despite its storied origins and high-impact look, the bolero looks great on a huge variety of people. "The square, angular shape and flat brim have a much more structured look that skews modern," say KIN/K designers, Ashley Cornil and Sara Brady. "Surprisingly, the bolero shape looks good on just about anyone because it balances the round characteristics of the face." KIN/K makes a lovely straw version ($125); if you want something that will work come fall, go for a felt bolero like this simple hat from Westerlind ($89).
You might have one or two felt-ier renditions of the cloche stashed away in your closet for winter, but consider a straw cloche for summer. The shallow brim offers you just enough shade to keep you cool, and the shape elevates your outfit from sundress and flats to "oh, just on my way to a garden party." Danielle Doty of New Orleans’ Trasy Diva advises that your cloche "should complement the your head shape with the brim resting just above the line of vision." She sells a few cloches in the classic retro style, like this straw cloche with a coral band ($35). Brookes Boswell has a more rustic-looking cloche ($198) with a slightly longer brim that can be worn flipped up or down, pictured above. If you want something more embellished (or more Jazz Age party appropriate), there are plenty to be found on Etsy.