In my personal archive of atrocious photographs, there is one that my mother has been legally threatening to post on Facebook every time she feels like I’m acting preachy or superior for the past twenty years. It features me standing in our suburban kitchen wearing a pair of platform sandals with a 3- inch foam sole, bottom-sagging JNCO jeans that were so capacious they could have doubled as nappies for a set of quintuplets, and; the crowning glory; a brown corduroy bucket hat. I’m smiling and waving peace signs at the camera like I know I’m streets ahead of the fashion pack and you mere mortals can’t comprehend my superior sense of style.
My mother was laughing knowingly when she captured me in this exact moment, shaking her head and saying something along the lines of “you’ll pay for this when you’re older, Harper.” Mum was right, like mothers often are. I avoided bucket hats like the plague for the better part of two decades. When I got my first assistant position at Style Compass USA, I swore to myself that once I entered the industry professionally, I would never; under any circumstances; wear even the remotely 90s-inspired trends my middle school self worshiped.
Bucket hats would be right there alongside butterfly clips and roll-on body glitter as far as this stylish lady was concerned. Mascara liquified onto cheeks?
Cool, trend forward.
Double denim with buckle boots?
Sure, why not? Bucket hats?
Hell no. “I mean,” I once told an intern who started quivering at the mention of low-rise jeans, “Fashion repeats itself, but some trends should simply remain in the decade they were destroyers in.” Spoiler alert: they did not remain. Flash forward to August of last year. I was covering a Supreme X collaborations pop-up in Williamsburg when I first spotted them lurking out of the corner of my eye.
Bucket hats. On children of the generation after mine. Children who were too young to remember the trauma that was early aughts fashion yet were proudly donning the crown jewel of its low points as if it were some coveted status symbol.
On adults. Influencers, bloggers, actual stylish people who got real jobs and knew how to respect themselves. Who I grew up with and somehow managed to forget their fashion morals along the way. “It’s ironic,” my friend Zoe told me when I text her begging for reassurance that those around me hadn’t spotted my presence. “They’re wearing them ironically.” Yeah, no.
Irony and I have a funny relationship when it comes to clothing. Wear something absurd enough for long enough and it stops being ironic, it just becomes what you wear. There’s a fine line between “I’m wearing this bucket hat to make a statement about ironic trends repeating themselves” and “I like the way this bucket hat looks so I’m gonna wear it” and that line fades the more times you wear it.
Let’s just say bucket hats became an unfortunate obsession of mine over the autumn and winter. I held out for 365 entire days before I finally caved and bought my first replacement from The Iconic. It wasn’t Vogue doing it’s part to rehabilitate my perspective on 90s-inspired trends; though they most definitely tried.
It was New York Fashion Week. It was also rainy. It had been raining all week which is the worst time to discover your hair does not react well to humidity + hat head + four days straight of dry shampoo.
I’d already been snapped twice by street style photographers that morning trying to rock what was supposed to be my signature messy haired wave but instead looked more wind attacked Demon Slayer villain. I was picking up my bags at a boutique in SoHo before they ran down to their next show when I saw it. A sleek black bucket hat made of canvas with hardly any branding at all.
You know those angels and demons on your shoulders that talk to you when you’re trying to make a life decision? The angel whispered sweet nothings into my ear about how this hat would cover up my hair debacle and no one would even notice. It was still raining.
Hell, I could even argue that it was a fashion emergency styling choice as opposed to me buckling and giving into upper-90s trends. The demon countered with “How will you explain to Becky text, Lisa when they see you posting another cliché selfie with a bucket hat on?” Reader, I bought it. Paid forty-seven dollars and a fraction of my soul later, I was trotting around the streets of NYC wearing public for the first time since my junior year of high school.
I didn’t give myself time to process that I’d bought a bucket hat. What I couldn’t believe was that I actually liked it on. It actually complemented my face rather than hiding it like the handy-dandy bag I felt it served as in my original photo.
It wasn’t overpowering my outfit and actually added to my chic-factor. When I caught a glimpse of myself in the storefront window I didn’t cringe. I nodded approvingly at my reflection like she was my own daughter.
What. The. Actual.
Fuck. It took me awhile, but I eventually caved and snapped a mirror selfie wearing it, pairing it with my now-signature tiltedswagger pose and captioning it with something groan-worthy about how I’d become my own cliché. The amount of likes and sweet, sweet engagement it got would’ve made my past self proud.
My editor Katherine text me that day, saying simply: “Bucket hat? Bold move. It works though.” Allow me to explain; when Katherine texts you that something you wore was a bold move and you know she’s stopping to type out compliments rather than just scrolling past you, you have basically reached Editor Oprah status.
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As someone who has made a career out of tearing people’s fashion choices apart I’m admittedly shocked by how many times I’ve worn my black bucket hat since that life-changing purchase. I own three now. The Catalyst, of course.
But also; dig me, a cream-coloured cotton bucket hat that I tell myself is “Hamptons chic” versus “I stole this from my older brother and thought he wouldn’t notice.” And; god help me; a dusty rose corduroy number that I recognise full well is from the same mill that made my 1997 disaster. But hear me out when I say that these are not your mama’s bucket hats. Yes, they might look similar at surface level.
But we are styling them to death completely differently than they were a decade or two ago. For starters, my closet circa 2005 was devoted entirely to items that could be considered an homage to Kid ‘n Play’s Funhouse. Oversized everything.
Giant trainers. Literally every accessory store sold shirts with charming puffy quotes on the back that I owned multiples of. Now, I wear my hats with tailored jeans and slim-fitting shirts.
I let the hat be my one nod to trend repeat and keep the rest of my outfit decidedly lowkey. I wore that cream bucket hat to meet with the publicists of a pretty big clothing brand last week. Straight-leg black trousers, fitted white t-shirt, blazer.
All fairly neutral pieces that wouldn’t be giving too much of my style game away on their own, but the hat added that extra something that took my outfit from plain to purposely lived-in cool. I got three compliments before lunchtime, one of which was from the fit queen carrying a full Celine bag who literally NEVER gives out fashion plaudits. On the weekends, I’ve even found myself wearing them with sundresses (again, not too flowy or voluminous of a silhouette) and even some cutoff shorts with an oversized linen button up; sleeves half rolled up, top two buttons undone, Very Main Character of The Island vibes.
As long as you’re keeping the rest of your outfit somewhat streamlined and intentional, I promise you cannot go wrong. My black one has quickly become my go-to airport style garment. Last month I flew to Miami for a brand launch and wore it with black leggings, an oversized grey sweatshirt, and minimal gold hoops.
Relaxed but not too lazy, and it hid my inevitable air-travel hair meltdown. To my surprise, the PR director of the brand even stopped me to ask where I got it. Lord knows I’ll never live that decision down, but at least someone approves of it.
I will also say that bucket hats, contrary to popular belief, actually flatter just about any face shape. Mine being on the rounder side, the slight stiffness of the brim actually gives my face some nice angles. My friend Emma has a more angular face and sticks to looser, more relaxed styles that soften her features.
They also happen to work on any hair length. I’ve seen my friend Marcus rock them with his buzzcut and my coworker Jessica with her waist-long curls. Trust me, there’s a bucket hat out there for you.
Now, this isn’t to say there still aren’t some bucket hat rules. Please do NOT wear anything that looks remotely like you scraped your local Foot Locker together in the late 90s. Stay away from floppy, slouchy styles that lean too much into “what the kids are wearing these days” because trust me, it just comes across as dad wearing a toddler’s beach hat.
And PLEASE FOR THE LOVE OF EVERYTHING HOLY UNDER THE SUN, no bucket hats with suits in the summer. I cannot stress that last one enough. If you’re going to do bucket hats, please do it right.
Your material matters. Cotton and canvas are always going to be your safest bets. Denim is okay if you’re not wearing denim on top (double denim plus denim bucket hat is Canadian tuxedo levels of hard) corduroy can work in the autumn if you stay away from the brighter colours and pair it with the right items.
Nylon or other technical fabrics can easily autumn into “trying too hard athleisure” territory OR be incredibly on-trend and stylish depending on how you style it.
Speaking of styling it…a few weeks ago I caught myself scouting out straw bucket hats at my local farm-supply store.
Paused cart mid-roll and said hell no.
Not today, bucket hat trauma. There may be a line I won’t cross with these and beachwear is it. What I wasn’t expecting about my bucket hat journey is that I don’t give a shit if people hate them on me.
There’s a part of me that knows my older, slightly cooler self is projecting midlife crises onto an innocent head accessory and another part of me that thinks I just survived low-rise jeans the first time they were popular so nothing will ever faze me again. But mostly I think; and this is what I want you lovely people to take away from my tale of woe; not everything in fashion needs to be serious. I can enjoy wearing a tacky ass hat and still love fashion.
Trends stop being ugly because we decide to look at them differently. Last week my mum and I were grabbing dinner and I was proudly rocking my black bucket hat with a simple slip dress and my go-to stack of gold bangles. She raised an eyebrow at me, took a bite of her salad and said “Haven’t you worn that hat before?
The one you swore was the single worst thing you’d ever worn?” “No Mum,” I said indignantly. “I wore a brown one in high school. This is completely different.” She just chuckled that smirk my at knowing mum chuckle she’s probably had for years. “Mmhm,” she replied, pulling out her phone. “Should I post that picture now or wait till your birthday?”
