The Case for Dressing Like a Weirdo

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My best friend, Taelor, was probably what pushed me over the edge into dressing like a weirdo. Shortly after we met in World History sophomore year, we agreed to attend the Fall dance together, him in devil horns and a flame shirt, me in a giant white tutu, halo, and wings.

From then on, it was go-go boots, pleated skirts, 70’s polyester for days. I only shopped at thrift stores and wore things that were interesting. Most of the kids in our high school bought striped sweaters from the Gap and flared jeans. Taelor, me, and our gaggle of friends just dressed however we wanted. Every so often, one of my more conventionally-attired classmates would walk up to me and say, “I love your ____, I wish I could pull that off.”

I always felt sad for them. It was like they assumed I had some kind of secret well of confidence that would allow me to wear whatever I wanted. The secret is that dressing weird makes you more confident.

That may sound backwards. But I was listening to an old episode of the Hidden Brain podcast this weekend where Francesco Gino of Harvard Business Review talked about people who practiced “positive deviance.” These people succeed by breaking the rules. In one experiment, students were made to perform karaoke in front of their classmates. Some had to wear a silly bandana while doing it and some didn’t. Those who wore the bandana actually performed better and stayed on key more than those who didn’t.

Think about it this way. If I walk into a meeting dressed in normal business wear, I code myself as just one of the group. If I walk into a meeting with something slightly off—dressed too casually or too formally, wearing sneakers or something, it’s kind of a power move. I can break the rules.

Reclaiming my old sense of fashion has been difficult for me in adulthood. The stakes seem higher than in high school. But every time I put on a bright lipstick, a weird legging, or a bold shoe, I feel more confident. I feel more myself.