I Spent a Week Styling a Pillbox Hat, and Now I'll Never Break These 3 "Rules"
I have always considered myself aggressively anti-hat. Not in a dramatic way—just in a this is not for me way. I’ve spent years telling myself my head is too big, my face too round, my proportions too off. Hats, in my mind, were either for people who look cool no matter what or for emergencies involving bad weather and worse decisions. Pillbox hats, specifically, lived in a very special category of intimidation: elegant, structured, historical, and clearly not designed with my anxieties in mind. They felt like they required posture, poise, and a personality I wasn’t sure I had access to.
So naturally, I decided to wear one every single day for a week. During Copenhagen Fashion Week. In public. In front of street style photographers. Insert Jemima Kirke "What the hell, sure" meme here.
The hat in question was the Gigi Burris Laura pillbox—clean, sculptural, and deceptively simple. Burris, who trained as a milliner at Parsons and still blocks each hat by hand using centuries-old techniques, is obsessive (in the best way) about proportion. The Laura’s shape is intentionally precise—designed to sit just right, not overwhelm—which I only appreciated after actually putting it on. What looks severe on a shelf suddenly felt grounding. Intentional. Like the outfit had a point of view, even when the rest of me didn’t.
Copenhagen Fashion Week turned out to be the perfect testing ground. As Coco Schiffer—stylist, influencer, and newly minted pillbox codesigner with Burris—told me during dinner last Copenhagen Fashion Week that confidence doesn’t come before you try something bold; it comes after you repeat it. If you wan't to be a hat person, just put on a hat!
By day two, the hat stopped feeling like a “moment” and started feeling normal. By day three, I wasn’t thinking about my head size or whether the hat looked right. I was just wearing it (and getting stopped for street style photographers, I might add!).
The timing felt especially fitting given that Schiffer and Burris had just launched their pillbox collaboration capsule—designed with real wardrobes in mind, not special occasions. Their shared philosophy is refreshingly anti-precious: pair a structured hat with everyday pieces, don’t overthink it, and let repetition do the work—or, as Schiffer might say, make everything else boring on purpose.
By the end of the week, the pillbox had quietly dismantled my long-held belief that I “don’t wear hats.” Turns out all it took was one well-made pillbox, a city full of good tailoring, and the willingness to just start.
How to Style a Pillbox Hat
Rule #1: Confidence Is Key
Confidence, more than anything else, is what makes a pillbox hat actually work. Hat designer Gigi Burris says it best: “Confidence is the only rule—when you walk out wearing a hat confidently, you shine, and the hat does not overpower you or any other part of the look.” I noticed this almost immediately during my week of styling one—once I stopped fussing over whether the hat was too much and just wore it like it belonged there, the whole outfit fell into place. The hat stopped feeling like a statement and started feeling natural.
Just like Burris predicted, the compliments came quickly. “Once you begin receiving compliments on your hat, which is inevitable, you will feel empowered to style it over and over again,” she explained. Turns out confidence isn’t just the first rule—it’s the one that makes all the others possible.
Rule #2: Keep Balance in Mind
When it comes to styling a pillbox hat, balance matters more than following any hard-and-fast rules. Schiffer sums it up perfectly: “I don’t really believe in strict rules, but I do believe in balance. If the hat is doing something, the rest of the outfit should calm down.”
That mindset became especially helpful as the week went on. Pairing the hat with clean silhouettes and familiar, unfussy pieces made it feel intentional rather than tacky. Schiffer warns that things can quickly tip into costume territory when everything is dressed up at once—“like you’re trying too hard”—and she’s right. Letting the hat have its moment while keeping the rest of the look grounded is what makes it feel modern, wearable, and effortless.
Rule #3: Avoid Overstyling
The quickest way to make a pillbox feel intimidating is to overstyle everything around it—structured dinner jacket, pointed toe shoes, and precious pearls might be a no-go. Schiffer is a big believer in keeping things a little undone, especially when it comes to hair. “A low bun, loose hair, or undone texture keeps pillboxes from feeling precious,” she says, calling them a “bad hair day’s best friend.”
That relaxed approach extends to the rest of the outfit, too—tailored pants, denim, loafers, and other everyday staples help ground the look. When everything else feels wearable and familiar, the hat stops reading as a special-occasion piece and starts acting like a shortcut: instant polish, without the effort.
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