I Dedicated a Week to Styling a Pillbox Hat, and Now I'll Never Ignore These 3 "Guidelines."

      I have long regarded myself as firmly against hats. Not in an exaggerated sense—more in a way that simply states they’re not for me. For years, I convinced myself that my head is too large, my face too round, and my proportions off. To me, hats seemed like they were for people who could pull off any look or meant for dire situations involving inclement weather and poor choices. Pillbox hats, in particular, fell into a uniquely intimidating category: elegant, structured, historical, and clearly not made for someone with my insecurities. They seemed to demand a level of posture, composure, and a personality I wasn’t sure I possessed. So, naturally, I decided to wear one every day for a week. During Copenhagen Fashion Week. Publicly. In front of street style photographers. Cue the Jemima Kirke "What the hell, sure" meme.

      The hat in question was the Gigi Burris Laura pillbox—clean, sculptural, and deceptively straightforward. Burris, who trained as a milliner at Parsons and meticulously blocks each hat by hand using time-honored techniques, is delightfully obsessive about proportion. The precise shape of the Laura is designed to balance perfectly without overwhelming, an insight I only gained after trying it on. What appeared severe on a shelf suddenly felt grounding. Purposeful. It gave my outfit a perspective, even when I didn’t feel I had one. Copenhagen Fashion Week proved to be the ideal environment. As Coco Schiffer—stylist, influencer, and newly co-designer of the pillbox with Burris—shared with me during dinner at last Copenhagen Fashion Week, confidence doesn’t precede bold endeavors; it follows from repetition. If you want to be a hat person, just wear a hat! By day two, the hat transformed from a “moment” into a normal part of my attire. By day three, I stopped worrying about my head size or if the hat suited me. I was simply wearing it (and getting approached by street style photographers, I might add!).

      The timing was particularly fitting as Schiffer and Burris had just launched their capsule pillbox collaboration—designed with everyday wardrobes in mind rather than just special occasions. Their shared philosophy is refreshingly pragmatic: combine a structured hat with casual pieces, don’t overthink it, and let the repetition do the work—or as Schiffer might express, intentionally make everything else mundane. By the end of the week, the pillbox had quietly dismantled my long-standing belief that I “don’t wear hats.” It turned out that all it required was one well-crafted pillbox, a city rich in tailoring, and the willingness to take that first step.

      ### How to Style a Pillbox Hat

      **Rule #1: Confidence Is Key**

      Confidence, above all else, is what makes a pillbox hat work effectively. Hat designer Gigi Burris articulates it best: “Confidence is the only rule—when you step out wearing a hat with assurance, you shine, and the hat neither overshadows you nor any other aspect of your look.” I noticed this almost immediately during my week of wearing one—once I stopped fretting about whether the hat was too much and simply wore it as if it belonged, the entire outfit came together. The hat stopped being a statement and began to feel natural. True to Burris's prediction, compliments came swiftly. “As soon as you start receiving compliments on your hat, which is unavoidable, you will feel empowered to style it repeatedly,” she explained. It turns out confidence isn't just the first rule—it’s the one that enables all the others.

      **Rule #2: Keep Balance in Mind**

      When styling a pillbox hat, balance is more significant than adhering to strict guidelines. Schiffer articulates it well: “I don’t believe in strict rules, but I do believe in balance. If the hat is making a statement, the rest of the outfit should be more subdued.” This mindset became increasingly useful as the week progressed. Pairing the hat with clean lines and familiar, uncomplicated pieces made it feel intentional rather than gaudy. Schiffer cautions that everything can quickly veer into costume territory if overdone all at once—“like you're trying too hard”—and she’s correct. Allowing the hat to be the focal point while keeping the rest of the look grounded is what makes it feel contemporary, wearable, and effortless.

      **Rule #3: Avoid Overstyling**

      The easiest way to make a pillbox seem daunting is by overstyling everything around it—think structured blazers, pointed shoes, and delicate pearls that may not work well. Schiffer advocates for maintaining a slightly untamed essence, especially regarding hair. “A low bun, loose hair, or a relaxed texture prevents pillboxes from feeling too precious,” she explains, referring to them as “the best friend of a bad hair day.” This laid-back