Memoir: my first hat transformed me from awkward teenager into fashion Zelig. I still use them as a disguise

The black hat answered my wanderlust. With it on, I could be a Quaker or a mind reader, Françoise Hardy or Bianca Jagger. It was a shortcut to my idols. The crown was collapsible, but the brim was not. Stiff and sure, it shadowed my face and served me well in a rainstorm or as I smoked by iron gates in a trench coat. It functioned like a hedge fronting a mansion, or dark glasses on the tired face of a gangster. It allowed me privacy and decoration. I craved both. The hat, with its four-inch brim, took up a lot of space. It was an invitation to look, but one issued by a recluse.

As a child, I was impossible to dress—I’d insist on wearing a nightgown to school, or wearing the same outfit for a year. In high school, instead of a prom dress, I wore my grandfather’s midnight-blue velvet tuxedo jacket—with no pants. My approach to fashion is this: I ask myself, am I a girl today, or a boy? Warren Beatty, all hair and strut and shirt unbuttoned, or Debbie Harry as Cleopatra? My icons are often androgynous: Patti Smith in her skinny-tie uniform; that slice of tenor genius, David Bowie, in his glam-rock space suits and heels and avant-garde kimonos, lightning bolt on his face. Fashion is what you decide to be in that moment in time.

The hat, like a moustache or a wig, is a flamboyant prop for transformation and disguise. It lets you simultaneously appear and disappear. You are suggesting other selves: the trucker, the showgirl, the thief.

I have spent thousands of hours trawling flea markets, yard sales, thrift shops, and the closets of my beloveds, looking for, in hunting terms, trophies: my father’s fur trapper with the Cyrillic script on the tag, my grandfather’s forest-green fedora with the yellow feather, the Tyrolean I found in a barn on the East Coast, the beaten-up Portis, the toques, the bowlers, the berets, the caps. Some finds are sentimental; others are for colour, shape, fit. My closet is now overflowing with hats—and yet, when I walk into a jumble shop, I always look to that top shelf where the hats sit, implying possible lives, wondering which one to pick.

I still have that wide-brimmed black wool hat from my mother. I still wear it for the fantasy it offers and its precise expression of where I was in time when it was given to me. Fashion, at its most evocative, is autobiography—both real and invented.

Claudia Dey is a writer and fashion designer for Horses Atelier in Toronto.

Hair and makeup by Blair Petty for Tresemmé Hair Care/judyinc.com