Our Big Fashion Month Takeaway Is That We All Need Personality Hats

If you don’t think of yourself as a hat person, the extravagant headpieces spotted on the runways this Fashion Month might have sent you into an identity crisis. See: the cowboy hats at Moschino, feathered military caps at Prada, Altuzarra’s pillboxes, Chanel’s floppy sun hats, and slouchy leather beanies at Vuitton. It’s enough to make you want to reconsider your stance on flattened hair — and have some more compassion for your “weird” head shape — but the larger message the Fall/Winter 2024 runways are sending is that now’s the time to pick a personality hat.

Serious or silly, your headgear, like the rest of your ‘fit, should play a part in expressing to the world exactly who you are. That’s why Julia Knox of East Village Hats prefers the term “character hats” to refer to the pirate tricorns and Bridgerton-style headpieces she says have been all the rage recently. Playing a role — even if that role is simply yourself — requires the right costume and accessories, which could be why Knox and her small team of milliners have received more custom requests this year than ever before, she says.

Another contributing factor might be growing interest in developing one’s personal style as a response to the revolving door of “-core” trends. A ball cap embroidered with a logo or pithy phrase says one thing; a sequined swim cap says far more. (Just think of how you’d view someone in a fedora.) And in this era of deep focus on letting your outsides communicate your inner life, what you pair with your crowning glory adds to the story. Take Jalil Johnson, the fashion-office coordinator at Saks, who says he often reaches for his Amy Downs knot cap or a Jenny Walton straw dome to add punctuation to a well-crafted outfit. In your styling, he says, you can go on-the-nose by pairing a pillbox with period-correct, Jackie O-ish skirt suit, gloves, and kitten heels. Or take the opposite route by juxtaposing a delicate Gigi Burris hat with a structured, more masculine silhouette.

Diamond Mahone Bailey, a stylist who’s worked with Erykah Badu, also suggests operating in a similar set of extremes by letting your chapeau shine with a minimalist outfit or going all in and over-accessorizing to “make it fancy.” But to source your personality hat, Bailey offers the additional recommendation of shopping vintage; she says she’s built up an impressive collection of unique vintage headdresses picked up from thrift stores around the world. (Her favorite milliner is Philip Treacy, who designed the veiled fascinator Rosamund Pike recently wore to conceal a skiing injury on the Golden Globes red carpet.)

Whatever character hat you choose, it should feel distinctly you — or even an idealized you. (Which is another reason why Bailey suggests shopping secondhand — because you’re far less likely to come across someone with the exact same one). After all, the most memorable examples of how a hat can accentuate and even elevate an individual often come from a place of romance and fiction. So even though it might take some work to figure out if you’re more of a cowboy or a cloche, try them all on — and don’t forget to embrace the fantasy.