Style 911: One Hat To Rule Them All

Here is my dilemma: I live in a super sunny state, and I have pretty bad light sensitivity due to chronic migraines. As a result, I frequently leave my house wearing sun glasses and a baseball cap to shield my eyes. Unfortunately, I cannot pull off the baseball cap look at all! Do you have any recommendations for cute and/or fun hats that provide some shade? — Martha

Hats are so tricky, but I commend your desire to shelve the sunglasses-baseball-cap-hide-me-from-paparazzi look in lieu of something a little more fun. The big, floppy sunhat is underrated. They are not for the self-conscious. If you make the decision to leave your house in a hat, you’re committing to the Look of a hat. Summer is the best time to dip your toes in these choppy waters. Winter hats command serious attention, and those big felt brimmed fedoras that you see plopped atop the heads of Forever21 mannequins tiptoe too close to Olsen-twin-emulation for my blood.

I could point you towards a wide swath of baseball hats, in fun prints, but eh. Save those for the fall! Save those for morning runs and late-night jaunts to the grocery store. If you’re going to put a hat on your head, just own it. Wear a damn hat. Here’s a few that I found that manage to be statements without hopping atop a table and shouting into a bullhorn.


From L-R: Goorin Bros “Mrs. Franklin”, $55; Goorin Bros: “Mrs. Maines”, $160

These are your formal hats. This is what you could wear to some sort of daytime party event, or a wedding, or just if you’re feeling fancy.


From L-R: Urban Outfitters “Mexicali” Straw Panama Hat, $34; Oasis Asymmetric Hat at ASOS, $27

Now we veer into everyday territory. These are structured enough so that you don’t feel like a Coachella castaway, but casual enough so that you can wear them with pretty much everything. Yes, I know they are fedora-adjacent. Yes, I know fedoras are horrible. But, rendered in straw, with a kicky ribbon around the brim, they are less so.


From L-R: Straw Floppy Hat With Thin Ribbon Trim at ASOS, $27; Floppy Straw Hat at Forever21, $14.90 

And now, for your everyday hat. These are fun, right? Kicky, even. You can wear them to the beach, and then stuff ‘em in your bag when the sun goes down. You can wear them with shorts. You can wear them with a dress. You can put sunglasses on and wear them however you think they should be worn. In these things, the world is your oyster.

Got a burning style question? Need to know how to wear those knee high gladiator sandals or that fur bikini you just bought? Email [email protected] and I will do my best to help!