1Panama Hat

Though technically from Ecuador, this classic style made it big when Teddy Roosevelt wore one to visit the Panama Canal. Sold in many shapes but most popular as a fedora, what makes it a Panama is the use of Toquila Straw. It’s an easy, laidback, summery look with an appealing borrowed-from-the-boys vibe. J.Crew white Panama hat, $58 at J.Crew.
2Panama Hat

Though technically from Ecuador, this classic style made it big when Teddy Roosevelt wore one to visit the Panama Canal. Sold in many shapes but most popular as a fedora, what makes it a Panama is the use of Toquila Straw. It’s an easy, laidback, summery look with an appealing borrowed-from-the-boys vibe. J.Crew white Panama hat, $58 at J.Crew.
3Sun Hat

The ultimate topper for a glamorous sun goddess—think Jennifer Lopez—a floppy sun hat is all about tropical style. Eugenia Kim “Greetings From…” hat, $475 at Nordstrom.
4Sun Hat

The ultimate topper for a glamorous sun goddess—think Jennifer Lopez—a floppy sun hat is all about tropical style. Eugenia Kim “Greetings From…” hat, $475 at Nordstrom.
5Gambler Hat

If the straw cowboy hat feels too cliché, try a gambler hat—defined by the oval crown and flatter brim profile—which offers a more modern and unexpected take on a Western style. Free People ‘Dean’ straw hat, $400 at Free People.
6Gambler Hat

If the straw cowboy hat feels too cliché, try a gambler hat—defined by the oval crown and flatter brim profile—which offers a more modern and unexpected take on a Western style. Free People ‘Dean’ straw hat, $400 at Free People.
7Fedora

Its reputation has been badly bruised by certain internet cretin types, but the thin-brimmed fedora is a classic that adds instant sophistication when deployed properly. Think of it like red lipstick—perfect as the final touch on a well-considered look. Maison Michel ‘Virginie’ straw fedora hat, $695 at Forward.
8Fedora

Its reputation has been badly bruised by certain internet cretin types, but the thin-brimmed fedora is a classic that adds instant sophistication when deployed properly. Think of it like red lipstick—perfect as the final touch on a well-considered look. Maison Michel ‘Virginie’ straw fedora hat, $695 at Forward.
9Visor

The latest hipster hit from the ’90s to make a comeback is the humble visor, upgraded with new materials and colors. Pairs well with the similarly ironic-but-not-ironic fanny pack. Shimmered straw visor, $32 at Anthropologie.
10Visor

The latest hipster hit from the ’90s to make a comeback is the humble visor, upgraded with new materials and colors. Pairs well with the similarly ironic-but-not-ironic fanny pack. Shimmered straw visor, $32 at Anthropologie.
11Boater Hat

This flat-topped, flat-brimmed hat has a dandy-ish vintage appeal, associated with barbershop quartets and gondoliers. The degree of difficulty for pulling it off is high, but when it works you’ve basically won at summer. Janessa Leoné ‘Klint’ hat, $188 at Janessa Leone.
12Boater Hat

This flat-topped, flat-brimmed hat has a dandy-ish vintage appeal, associated with barbershop quartets and gondoliers. The degree of difficulty for pulling it off is high, but when it works you’ve basically won at summer. Janessa Leoné ‘Klint’ hat, $188 at Janessa Leone.
For all the fuss we put into dressing, most accessories are hard to mess up. Jewelry can’t help but add to an outfit, and almost any pair of sunglasses will make the wearer look cooler. (It’s science!) But hats are uniquely tricky, with their myriad shapes and materials. Maybe that’s why we love them—when they work, it’s taking your summer style to another level.
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