how to wear a bucket hat

I Figured Out How to Wear a Bucket Hat

As a serious, semi-sophisticated adult human woman, no less!

In Why, Though?, digital editor Jennifer Berry test-drives the trendiest of fashion trends that would make any reasonable person ask, “Is it possible to wear this if one is not a Hadid?” So far, she’s been shocked to discover she enjoyed wearing bike shorts and a fashion puffer, but was considerably less enthused about athletic sunglasses. Most recently, she unlocked the key to wearing the slime green trend in real life, and now, she’s navigating how to wear a bucket hat.

If you told me six months ago that in the year of our lord 2019, I would be brainstorming how to wear a bucket hat, I would have asked you to pray for my swift and speedy recovery because there would be no explanation other than sudden head trauma. But, here we are, with me eating my words after once again falling victim to a trend cycle that has seduced me into trying chokers, bike shorts and electric acid green in my, ahem, 30s. (I never did succumb to micro-sunglasses, though, and would like that inscribed on my tombstone.)

Like athletic sunglasses before it, the humble bucket hat is an item that had its roots firmly planted in utility before making its way into pop culture, and eventually, fashion. As a child, I remember seeing canvas bucket hats on characters like my friendly, 50-something, granola-making, crocus-planting neighbour who never took her gardening knee pads off. My next memory of the bucket hat belongs 4ever to ’90s television icon Blossom whose black felt version with an oversized daisy brooch affixed to its turned-up bill was my tween dream. Then sometime in the mid-’90s, the preferred headwear of fishermen everywhere made its way into hip-hop style with rappers like LL Cool J and Jay Z sporting the floppy chapeaux with their football jerseys and Helly Hansen coats. 

 

 
 
 
 
 
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When the trend reappeared on the Spring 2019 runways of 3.1 Phillip Lim and Michael Kors in trippy colourful patterns and on the very attractive heads of celebrities like Rihanna and street-style pros like Susie Bubble, I was intrigued—the bucket hat is undeniably cute!—but cautious. Could I, an adult woman with a childishly round face, look anything but like I was in a Mayim Bialik circa 1992 Halloween costume whilst wearing one? Or worse, would I have to forgo all femininity and wind up looking like Wilson from Home Improvement?! I acquired a dusty rose corduroy version from Urban Outfitters (corduroy! My younger self wanted to be absolutely swaddled and mummified for all eternity in the ribbed fabric) and tried to make the bucket hat my own. Here’s what I learned. 

how to wear a bucket hat

OUTFIT #1: IN COMPLETE CONTRAST TO A LEOPARD-PRINT MIDI-DRESS 

I was aiming for “Milan Fashion Week street style” by pairing the sweet headwear with a comparatively sassy animal-print dress and black leather knee-high boots, but felt decidedly more “kooky art teacher” in this combination. When wearing this in public, I also encountered a familiar fashion beast that rears its ugly head when I try a trend I’m not sure is for me—sartorial imposter syndrome. I felt self-conscious in the hat, ready to breathlessly explain to anyone I crossed paths with en route to the office that I wasn’t actually wearing it IRL (“It’s for a test-drive!”), but I didn’t get so much as a second glance. 

 

how to wear a bucket hat

OUTFIT #2: A MONOCHROME MOMENT WITH A UTILITY WINK 

Like Kate Middleton loves head-to-toe green for St. Patrick’s Day, I love a theme and I embraced my pink lady moment in a blush belted denim jacket and matching rose bucket hat. This outerwear has become an MVP in my wardrobe since I snagged it on sale last Christmas (the only thing she loves more than a theme is a Zara sale), so I felt comfortable in this ensemble, worn with cropped mid-wash denim and snakeskin booties. But alas, I feared that the safari details on the jacket read a little too utilitarian and, when paired with the bucket hat, made me look like I was going from the office to a carp-catching expedition. 

 

how to wear a bucket hat

OUTFIT #3: A CASUAL FRIDAY OOTD THAT FELT LIKE ME 

Call me Goldilocks, but my third attempt at wearing a bucket hat in the real world was just right. The knit sweater with multicoloured stripes felt like something dear Blossom might have worn under a suspender dress (in the best way possible), while my now-beloved black lacquered fashion puffer and battered Levis injected the low-key combination with a certain edge. I liked how the rose of the bucket hat picked up the blush in the sweater. I was feeling the wave in my hair. But mostly, I just felt cute because like winning OOTDs before it, the special sauce for figuring out how to wear the bucket hat trend—or really anything you’re not sure you can “pull off”—is confidence. And that, my friends, is timeless. 

Photography by Mariah Hamilton. Hair and makeup in main image by Kim Creton for Charlotte Tilbury/R & Co/Plutino Group.

 

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