I Resisted Hats for Years—Now I Realize They’re the Ultimate Outfit Upgrade
The accessory I once avoided is officially my favorite styling trick.
For years, I treated hats like a phase I’d already outgrown. When the wide-brim styles of 2016 started resurfacing in everyone’s nostalgic Instagram carousels, I was instantly transported back to my own hat era—stiff felt brims, carefully angled selfies, outfits built around the hat instead of the other way around. An era that now feels suspiciously close to that infamous Heidi Gardner SNL sketch.
Somewhere along the line, hats stopped feeling intuitive. Not quite like me—which is ironic, considering my style leans bold, loud, and joyfully extra. I’ll happily pile on statement jewelry or commit to a maximalist coat without hesitation. But hats? Those felt like a styling puzzle I couldn’t quite solve. Sure, I’d grab a baseball cap on a bad hair day or a beanie when it was frigid—but those were functional choices, not fashion ones.
Then the street style from recent fashion weeks shifted something. Structured wool caps. Perfectly perched pillboxes. Playful, vintage-coded silhouettes that made even the simplest outfits feel intentional. Suddenly, hats weren’t filler—they were the focal point.
At the same time, the internet has been deep in its Love Story obsession, collectively revisiting JFK Jr.’s effortless ’90s polish—and, notably, his excellent hats. Every backward baseball cap, every Kangol, every sharply tailored topper has been screenshotted and dissected. It’s a reminder that a great hat has always signaled something: ease, confidence, a point of view. The right one doesn’t overpower an outfit—it anchors it.
The more I paid attention, the clearer it became: a hat doesn’t just finish a look; it sharpens it. It adds punctuation. It makes a simple outfit interesting and suggests you considered the full picture, even if you got dressed in five minutes.
I finally gave in, and now a cheetah pillbox from Lele Sadoughi has practically fused to my head. It works with everything—oversized tailoring, slouchy knits, lazy denim. A pink beret-pillbox has joined the rotation, too. It’s the fastest way I know to elevate a silhouette without adding bulk or fuss.
If you’ve been hat-hesitant like I was, consider this your sign. The right one doesn’t just top off an outfit. It transforms it.
