Baseball cap is a classic attribute of the American life. However, opinions here are split: it can be as much of a gimmick as it is a fashion statement. I say it depends on how you style it.
Baseball cap + old dirty T-Shirt + cargo shorts + flip flops = pass.
Baseball cap + oversized well-tailored coat + anything else = in.
Baseball cap + Patagonia fleece vest + AllBirds boat shoes = pass unless on a boat.
Baseball cap + flowy feminine dress + combat boots = in.
Baseball cap + cute animal = always in!
To summarize, it’s best to style your good ol’ headpiece with something unexpected. As illustrated here by Elizabeth Kuzyk, by Yasmine Eslami, and Jacina Almond, all of whom really know how to rock a cap. Silk skirts, high-heel boots and fine cowhide will get you as far from athleisure as possible. And that’s why it works!
I usually pair my caps with a big coat as pictured above, or a trench coat (more on that next week). And as for what’s underneath – I’m unbothered. Leggings and sneakers are just fine, as long as there’s a structured piece on top.