There’s a photo of me from 1997 that my mother still threatens to post on Facebook whenever I get too full of myself. In it, I’m standing in our kitchen wearing platform sandals with a 3-inch foam sole, impossibly wide-leg JNCO jeans that could have comfortably housed a family of four, and—the pièce de résistance—a brown corduroy bucket hat pulled low over my eyes. I’m flashing a peace sign and sporting the kind of smug teenage expression that suggests I believed this ensemble was the absolute pinnacle of fashion. My mother, bless her heart, snapped the picture while saying something along the lines of, “You’ll regret this someday, Harper.”
God, I hate when mothers are right.
For years, that bucket hat represented everything I wanted to distance myself from in my fashion evolution. When I landed my first assistant job at Style Compass USA, I made a solemn vow to myself: no matter what unholy trends from my youth were resurrected by the cyclical nature of fashion, bucket hats would remain firmly in my “never again” category, right alongside butterfly clips, roll-on body glitter, and those weird plastic tattoo chokers that looked like we were all wearing miniature Slinkies around our necks.
“Fashion is cyclical,” I’d tell interns sagely, “but some things should stay dead and buried in the decade that spawned them.”
Then, last summer, while covering a streetwear pop-up in Williamsburg, I spotted them. Bucket hats. Everywhere. Not just on Gen Z kids who weren’t alive to experience the trauma of the original trend, but on cool, fashionable adults who should have known better. People with good jobs and apparent self-respect. People my age who lived through the first bucket hat apocalypse and somehow didn’t learn their lesson.
“It’s ironic,” my friend Zoe said when I called her in a panic. “They’re wearing them ironically.”
But here’s the thing about irony in fashion—wear something ironically long enough, and suddenly you’re just wearing it. Full stop. There’s a thin line between “I’m wearing this bucket hat as a commentary on nostalgic fashion cycles” and “I’m wearing this bucket hat because I legitimately like how it looks.” And that line gets thinner with each wearing.
I managed to resist for exactly eleven months and seventeen days. What broke me wasn’t high fashion’s endorsement—though certainly Prada and Loewe tried their best with their runway versions—but something much more mundane. It was a rainy Tuesday in April, my fourth day of Fashion Week coverage, and my hair was staging a full-scale rebellion after being subjected to humidity, hat-head, and too much dry shampoo. I’d already been photographed by three street style photographers that morning, and my usual “effortlessly tousled” look had morphed into something that could only be described as “possibly electrocuted.”
Standing in a boutique in SoHo, waiting for a presentation to start, I spotted it—a black canvas bucket hat with minimal branding. The practical, dark angel on my shoulder whispered: “It would hide your hair disaster. No one would know. It’s raining. You could pass it off as weather practicality rather than a trend submission.”
Reader, I bought it. Forty-seven dollars and a piece of my soul later, I was wearing a bucket hat in public for the first time since the Clinton administration.
The most disturbing thing wasn’t that I bought it; it was that I liked it. It framed my face in a way that was actually… flattering? It added a certain effortless cool to my otherwise pretty conservative outfit of straight-leg jeans and an oversized button-down. When I caught my reflection in a store window, I didn’t immediately cringe. In fact, I nodded in subtle approval.
What. Was. Happening. To. Me.
Over the next few weeks, I found myself reaching for the hat with alarming frequency. I posted a mirror selfie wearing it, captioned with a self-deprecating joke about becoming everything I once mocked. The response was disturbingly positive. Katherine, my editor, texted me: “Bucket hat? Bold choice. Works though.” Coming from Katherine, this was essentially a standing ovation.
As a woman who has built a career partly on brutal fashion honesty, I feel compelled to admit: I’m now the proud owner of three bucket hats. The black canvas one that broke me, a cream-colored cotton one that I tell myself looks “Hamptons chic” rather than “failed rapper,” and—god help me—a dusty rose corduroy one that is distressingly similar to my 1997 original.
But here’s my defense (and advice for anyone else reluctantly considering this trend): 2025’s bucket hats are not your 90s bucket hats. The proportions have been refined. The materials have improved. And most importantly, we’re styling them completely differently.
My teenage self wore bucket hats with outrageously oversized clothing, platform sneakers, and enough Claire’s accessories to sink a small ship. Current me wears them with simple, streamlined pieces that let the hat be the one nostalgic element in an otherwise adult outfit. It’s about balance—the golden rule of incorporating any potentially questionable trend into your wardrobe.
Take last week, for instance. I paired the cream bucket hat with straight-leg black trousers, a fitted white t-shirt, and a tailored blazer for a meeting with a PR firm. The hat took what would have been a borderline boring professional outfit and gave it just enough edge to be interesting. I received three compliments before noon, one from a woman wearing head-to-toe Celine who doesn’t strike me as someone who gives out fashion approval freely.
For weekend wear, I’ve found that the bucket hat pairs surprisingly well with sundresses (keeping the silhouette simple and not too voluminous) or even with shorts and a slightly oversized linen button-down—sleeves rolled up, a couple buttons undone, very relaxed coastal vibes. The key is making sure the rest of the outfit feels intentional rather than like you’re wearing a costume from the “greatest hits of the 90s” party.
The black one has become my travel staple. On a recent flight to Miami for a brand launch, I wore it with black leggings, an oversized grey sweatshirt, and simple gold hoops. Comfortable but put together, and the hat hid the inevitable airplane hair situation. The PR director for the brand actually asked where I got it, which I took as validation of my surprising life choices.
I’ve also discovered that bucket hats are strangely versatile for different face shapes. My face is somewhat round, and the slight structure of the brim actually creates some helpful angles. My friend Emma, who has a more angular face, wears softer, more relaxed versions that soften her features. And they work on literally any hair length—I’ve seen them looking equally chic on my friend Marcus with his buzzcut and on my colleague Jessica with her waist-length curls.
There are still rules, of course. I draw the line at logo-heavy styles that scream “I raided my local Foot Locker in 1998.” Anything too floppy ventures into “toddler at the beach” territory. And please, for the love of all things holy, no bucket hats with summer suits unless you’re actively trying to look like you’re in a boy band reunion tour.
The fabrics matter tremendously. Canvas and cotton are the safest bets for a modern take. Denim can work if the rest of your outfit isn’t denim (double denim plus a denim bucket hat crosses firmly into Canadian tuxedo territory, and not in a good way). Corduroy is risky but possible in fall with the right accompanying pieces. Technical fabrics like nylon can go either sports-luxe cool or straight-up tacky, depending entirely on quality and styling.
To my absolute horror, I recently found myself eyeing a straw version for summer. I stopped myself, but only just. There are limits to my rehabilitation, and beachwear bucket hats might be mine. For now.
The most surprising thing about my bucket hat renaissance isn’t how much I like wearing them—it’s how little I care about the possible judgment. Ten years ago, I would have rather died than voluntarily revisit a trend I so thoroughly embraced and then rejected. Now, there’s something almost liberating about reclaiming a piece that once represented my most cringe-worthy fashion phase.
Maybe it’s a sign of getting older and caring less about arbitrary fashion rules. Maybe it’s that after surviving low-rise jeans the first time around, nothing can truly scare me anymore. Or maybe—and this is the conclusion I’m reluctantly coming to—fashion really shouldn’t be taken so seriously. Sometimes an ugly trend stops being ugly simply because we decide to see it differently.
Earlier this month, I was having dinner with my mother, proudly sporting my black bucket hat with a simple slip dress and chunky gold jewelry. She narrowed her eyes, took a sip of her wine, and said, “Isn’t that the same hat you wore in high school? The one you swore was the biggest fashion mistake of your life?”
“No, Mom,” I replied with all the dignity I could muster. “That one was brown corduroy. This is canvas. It’s completely different.”
She just smiled that irritating knowing smile that mothers have perfected over millennia. “Mm-hmm,” she said, reaching for her phone. “Should I post that old picture now, or wait for your birthday?”
Some things never change. But thankfully, how we wear bucket hats has. And if my mother does post that picture, at least now I can claim I was simply ahead of the 2025 trend cycle. By about 28 years.
