How Can I Wear a Hat with Sunglasses—and Make It Look Stylish?

Do you have a pressing style question that nags you every time you open the closet door—like can you wear white to a wedding? After Labor Day? To a Christmas party? Email your most problematic sartorial queries to editor@purewow.com and PureWow’s fashion editor, Dena Silver, will answer in a new column, Can I Really Wear That? 

The short answer is: Yes! Absolutely, but before we get to that, I just have one thing to say: Make sure you’re also wearing SPF!!!! 

OK, now that I’ve gotten that off my chest, I’m here to tell you that it is totally, 100 percent possible to get this level of sun protection on the beach while still looking like a functioning member of society. But it all comes down to the style of the hat and the shape of the frames that you pair it with. Note that the order of that is very important, as your hat will inform the sunglasses you should choose. Let’s get into it.

We can all agree that this is the sportier headgear option, and your frames should complement that fact...or at least exist in harmony with it. So this is not the time to go for frames that feel too glam (yeah, you might want to leave your jewel-encrusted Guccis behind). Instead opt for sunglasses that embody an athletic feel. In this case, a sleek aviator is a good pick, like Krewe’s super-streamlined option—that (bonus!) comes with extra sun protection. Or, go for an updated Wayfarer shape that feels slightly more feminine, like these rounded Ray-Bans that come in a sleek tortoiseshell (even Kate Middleton is a fan). Leaning into the sporty aesthetic will feel less like you’re on the run from the paps and more like you’re wearing this covered up combo for a reason.

As a baseball cap generally has a snug fit, you will definitely want to keep comfort in mind when selecting your frames. Krewe founder Stirling Barrett notes: “Generally speaking, steer clear of [pairs] that are too oversize or have too thick of temples, which could potentially make the hat and sunglasses uncomfortable to wear together.” 

By the way, you can (and should) let your cap be the statement piece with this combo. Might we suggest using it to brag about your newspaper of choice ($28)? Or maybe you want to lean into your newfound sporty aesthetic ($18)? If not, you could always shell out the big bucks for a designer iteration in a fine silk with a cute bow ($490).

Simply put, if you want to look—and feel—glamorous in a hat and sunglasses, go for a trendy woven topper.

Look for a style that has a grosgrain ribbon at the crown so it will be snug on your noggin—just like this country chic straw hat from Gigi Burris ($388) that will provide ample coverage from the sun. Wear it with a geometric pair of sunnies in classic black and white ($110) for a retro vibe. And yes, this is the perfect opportunity to match the ribbon on your hat, like this packable style with a black and white accent ($325), to your stark black cat eye sunnies ($350).   

If you want to really push the limits of this glam look, now is the time to try out a large, round style with pink lenses ($200) or oversized, angular wire frames ($11). 

But keep in mind fit is still extremely important when it comes to wearing a woven hat with shades. If the hat is too big, you risk losing it (and your glasses) with the next gust of wind; if the headpiece is too tiny, you won’t be able to fit anything under it, let alone your hair.

Also, consider the angle of your accessory. “The hat should always be worn a bit tilted back on your head if you’re going to wear sunnies. That way your sunglasses and the brim of your hat aren’t competing,” hat designer Eugenia Kim explains. This applies to a flat-top boater style ($23) or a more angular fedora shape ($44).

Note: Most of the straw hat rules will also apply to a trendy bucket hat ($23), if that feels more you. Just stay clear of pairing this particular style with yellow-lensed aviators—otherwise you’ll be channeling Fear and Loathing in Las Vegas.

Oh, and don’t forget to reapply SPF every two hours…