I recently read a great article about the eternal debate of form versus function.  What I have realized about myself is that as much as I would like to choose function, I am that kid who always takes the one cookie. (You know the infamous study, one cookie now versus two cookies later.) But I would only take the cookie if it looked good. No matter how amazing it smells or tastes. I couldn't eat black beans for years in my burritos because I hated how they looked. I hide ugly but amazing products and often won't buy them again because I don't like how the wrapper looks. I am, in essence, the worst.

So when it comes to sun protection, while I am deadly serious about function - I just will not do it if I don't like the way it looks (or smells!) With that in mind comes the dilemma of the baseball cap.

In windy Chicago, it can be tricky to wear my beloved wide brimmed straw hats. Definitely not for a day of boating, where the boat draft alone is enough to send the wrong topper flying off in the ether.

A good adjustable baseball cap is a lifesaver - it stays on, snug against your head and immune to all but the largest of gusts.

So, with an impromptu boat trip scheduled, I knew I needed to whip out my best cap game. I turned to Pinterest, as one does, looking for inspiration for how to look adorable while wearing a cap.  Here's what I learned.


A little curl goes a long way when it comes to looking cute with a ball cap. It flows outward from the tight restrictive brim in ripples that add just the right tousled effortlessness to the no-fuss cap look while still being charming.


Not just from a style perspective (although the distressed look is definitely in) it's also quite important for the brim to shape to your face, something that new hats don't have (unless you're intentionally rocking that flat brim style, in which case it must be crisp and shiny as a new penny.)


I like a mostly flat front with a little tilt at the end. If I could pull it off I'd basically wear a windshield over my entire face in sunglass form, but absent that you can't go wrong with aviators or an oversided cat-eye/wayfarer.


Here I layered my favorite sunscreen with a foundation with sunscreen, in addition to the hat and sunglasses.