Nothing says languorous poolside glamour like a billowy sunhat. The full-circle brim provides instant shade, while elevating the elegance factor—be it with a one-piece swimsuit, a maxi dress, or short shorts and tank. Keep a couple of sun hats in your closet, so you can change up brim widths depending on how strong the sun is.
A preppier take on the sun hat, this variation usually has a slightly more compact brim and works well for dressier occasions like garden cocktail parties. Embrace the summery sophistication by wearing it with a white silk tank and tailored wide-leg pants or a breezy linen dress or jumpsuit.
This is your go-to when you want to show off your killer ponytail, top knot, chignon, or braid while also protecting yourself from the sun. Get playful with texture here—a translucent colored brim and sleek leather band will give you a more contemporary aesthetic, while a woven straw pattern channels a subtler seaside spirit.
Long a favorite among painters, poets, beatniks, and otherwise bohemian folk—oh, and ’90s Michael Jordan—the beret is also beloved by the fashion world for its easy sophistication. Wear it with a turtleneck and flowing skirt, a sweater and jeans, or in a complementary shade to your go-to winter coat.
Whether your vibe skews closer to après-ski or Brooklyn hipster, beanies are the secret to mixing up your cold-weather wardrobe. A slouchy, fine knit or nautical watch cap pairs well with more casual denim outfits, while intricate knit patterns and voluminous pom-poms add personality to an outerwear-based look.
This classic has come a long way since it first sat atop the heads of boys peddling ‘papes in the early 1900s. Thanks to its cool, British aesthetic, it’s also become a favorite among the street-style scene. Wear it with simpler pieces to avoid costumey vibes, like cigarette pants, a fitted tee, and a moto jacket, or a slouchy sweater and jeans.
There’s something so deliciously ’70s about a great felt hat, whether it’s the quirky American styling of Annie Hall or the exquisitely French boho vibes of Jane Birkin and Brigitte Bardot. Either way, pair a felt fedora or floppy with something voluminous, like wide-leg trousers or a statement-sleeve maxi.