Consider the Novelty Hat

I grew up viewing hats as practical, outfit-ruining add-ons. A baseball cap to conceal a bad hair day. A tuque in the winter to keep the chill off. A wide-brimmed chapeau to protect my pale skin at the beach, while my naturally tan peers ran around in string bikinis. To me, the hat — in all its shapes and forms — was at best an innocuous nuisance and at worst a necessary evil. But recent events have inspired me to take all that back.

It started — as many great tales do — in an overpriced souvenir shop. On a trip to Scotland this past summer, I meandered into a touristy Edinburgh boutique to see a selection of touring caps lining the wall. A cousin to the newsboy cap and sometimes called a flat cap, the traditional menswear style has a tweed fabrication, a subtly rounded silhouette and a stiff front brim. I had always associated it with my late papa, who emigrated from Scotland in the ‘50s and sported the traditional style daily. Drunk off a jet-lagged-induced urge to treat myself and overwhelmed by a sudden sense of paternal nostalgia, I went against my better judgment (hats = no) and bought it.

As I walked out onto the cobblestone streets sporting my new purchase, I felt what I can only describe as the polar opposite of buyer’s remorse. For the rest of my trip, I couldn’t go anywhere without it. I paired it with a skirt and tights outfit. I wore it alongside a frothy green dress. Even my most bare-bones look — slouchy slacks and a thick long-underwear top — felt chic with my cool new cap. Because there was no utilitarian reason to wear it, I felt the possibilities of self-expression open up.

Styling success aside, I’ve found that wearing my novelty hat makes me more confident. Putting it on is an intentional getting-ready step that primes me for the day ahead. When I’m feeling friendly, I can tip my cap at people in an old-time-y, approving way. If I’m in a playful mood, I can take it off and bow to theatrically greet a friend. In my experience, wearing a hat just for fun is a way of embracing thoughtfulness in a time of unrelenting pressure to be fast-moving. Turns out, I’m not alone in that.

Emilia Petrarca reports in Harper’s Bazaar that the decline in popularity of hats reflects modernization in other areas. Prior to the 20th century, hats were a staple of nearly every outfit. But as the world evolved and human innovation hurdled on, not wearing a hat symbolized freedom, she notes.

It’s the relegation of a hat as an extra accoutrement, I think, that made me fear it. When you’re wearing a novelty hat, you’re saying something. You’re making a choice and standing behind it. Plus, there’s a unique element of vulnerability about an accessory that sits atop the head. It’s the first thing someone sees when they see you, it expands the space you take up and whether you like it or not, it can say a lot about your style. But when done right, this can be a great thing.

Perhaps that’s why the Fall 2024 runways were rife with statement chapeaux. Armani Privé presented slanted pillbox hats with XL pearls dangling on one end. Chanel showcased ultra-floppy wide-brimmed designs alongside effortless slouchy knitwear numbers (below). Christian Dior put an edgy spin on the Parisian beret with stud-adorned leather.

The street style across fashion month continued the cool-hat-craze, with front-row figures wearing everything from well-constructed caps to casual sporty iterations. The reason? Nothing is cooler than someone who is unafraid to step out in a head-turning novelty hat.

Think about it: Some of the most memorable moments of personal style involve unconventional headwear. Céline Dion’s backwards suit 1999 Oscars look was made all the more iconic with the addition of a Dior fedora. Pharrell’s giant 2014 Grammys hat solidified his status as an avant-garde style symbol. And Rihanna’s decision to wear a black beanie to the 2021 Met Gala subverted stuffy dress-codes of prestigious fashion spaces.

The verdict on the novelty hat

I’ve come to realize that hats are not hindrances, but harbingers of personality. A baseball cap is effortless and casual — or in the case of Kendall Roy, an under-the-radar indicator of class. A cowboy hat can be the ideal entry point into Western-wear and a symbol of age-old cultural significance. High-reaching statuesque styles, like a pillbox or a top hat, communicate polished self-assuredness. And in my case, the touring cap was a cheeky nod to my heritage, a fun play on gender norms and a playful challenge to bake into my routine.

So, take it from a reformed hat hater. Instead of writing off the accessory, consider what possibilities it could bring. It just might be the source of a style metamorphosis. At the very least, it’s an excuse to treat yourself.

The chicest novelty hat picks to shop now

Hanna Hats Irish touring cap

Made in Ireland, this handcrafted wool touring cap might be the ideal way to foray into statement hat territory. Thanks to its salt-and-pepper stitching, it leans into the vintage appeal of the design. Pair with a grey pleated skort for a collegiate-meets-old-school finish.

Eugenia Kim Emmanuelle in espresso

Eugenia Kim’s Emmanuelle hat puts a modern spin on the fedora. Because of its deep chocolate colour, satin ruched band and subtly pinched top, it puts a polished finish on the recognizable silhouette. Pair with plush wools for a cozy wintertime ensemble.

Collina Strada Vitelli purple plaid winter hat

Made of reclaimed yarns, Collina Strada’s sustainably crafted knit beanie is a pop of personality. Its imperfect finish gives it an organic appeal, while its multi-coloured hue keeps outfits interesting. If you like the style and want to go even more outside-the-box, try opting for the brand’s spikey knit iteration.

Lack of Color terracotta rancher

Do you need a terracotta-coloured rancher hat? Maybe not — and yet, this one feels like the right choice to make. Made of 100 per cent Australian wool, this winter-ready chapeau is meticulously crafted. From the pinched crown to the structured brim, it is polished, playful and slightly statuesque. Why not take it for a spin?

Gemsun Doris cap

Handmade with deadstock fabric, this lace-trimmed cap is a dainty statement. Adorned with gold polka dots, it’s an elevated-yet-whimsical pick that adds some romance to everyday ensembles. Style with mod capris, ballet flats and a leather trench for a feminine-leaning look.

Reitmans plaid bucket hat

Up the ante on the classic bucket hat with this fuzzy plaid pick. Made by Canadian brand Reitmans, it is both cozy and structured for cozy all-day wear. As a result, it’s the perfect everyday statement novelty hat. A neutral trench and knee-high boots will complete the fun-meets-professional aesthetic.