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💡 TLDR
Slay alert: I used to think pillbox hats were for people who looked effortlessly cool—or for when it’s 32 degrees and you’re wearing a trench coat like it’s a costume. Turns out, they’re basically the…
Slay alert: I used to think pillbox hats were for people who looked effortlessly cool—or for when it’s 32 degrees and you’re wearing a trench coat like it’s a costume. Turns out, they’re basically the ultimate confidence booster—until you try them. So I did. For a whole week. In Copenhagen. In front of street style photographers. Insert Jemima Kirke “What the hell, sure” meme here. The hat? The Gigi Burris Laura pillbox—clean, sculptural, and deceptively simple. Burris, a milliner obsessed with proportion, designed it to sit just right, not overwhelm. And once I actually wore it, I got it. What looked severe on a shelf suddenly felt grounding. Like the outfit had a point of view, even when the rest of me didn’t.
Copenhagen Fashion Week was the perfect test. As Coco Schiffer—stylist, influencer, and now pillbox codesigner with Burris—told me over dinner, confidence doesn’t come before you try something bold; it comes after you repeat it. 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 photos, I might add!). The timing felt especially fitting since Schiffer and Burris had just launched their capsule collection—designed for real wardrobes, not special occasions. Their philosophy? Anti-precious. Pair a structured hat with everyday pieces, don’t overthink it, and let repetition do the work.
The quickest way to make a pillbox feel intimidating is to overstyle everything around it—structured dinner jackets, pointed toe shoes, and pearls? No-go. Schiffer’s secret? Keep things undone, especially your 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.” The rest of the look? Tailored pants, denim, loafers, and other staples. Grounded, wearable, and effortless. Once the hat stops reading as a special-occasion piece, it becomes a shortcut: instant polish, without the effort.
Key points: Confidence is the only rule—when you walk out wearing a hat confidently, you shine, and the hat doesn’t overpower you. Balance matters more than rules: If the hat is doing something, the rest of the outfit should calm down. And don’t overthink it—pair structured hats with everyday pieces, keep things undone, and let repetition do the work.
💫 Share your confidence hacks below.
So, what’s your hat story? Share your confidence hacks below!
❓ People Also Ask
How do I style a pillbox hat without looking outdated?
Pair with modern outfits, avoid puffy fabrics, and keep hair sleek. Focus on clean lines and contemporary accessories for a fresh, updated look.
Can I wear a pillbox hat with bangs?
Yes, if bangs are swept back or styled to complement the hat. Avoid heavy layers that may clash with the hat’s structure. Keep the overall look balanced and cohesive.
💬 What do you think? Let us know in the comments! 👇