When I was sixteen years old, I bought a fedora. I was inspired by Humphrey Bogart in the movie The Big Sleep. In the film, Bogart plays Philip Marlowe, a cocky, private detective who solves a complex case involving blackmail and murder. But on the first day wearing my fedora, I discovered the mean streets of 1940s Los Angeles were child’s play compared to the cinderblock halls of a rural high school in 1986. Walking to first period, my fedora was yanked off my head and thrown in a garbage can by a group of burly seniors who looked like lumberjacks on their way to a sawmill. At lunch, members of the football team threw tater-tots at my hat and questioned my sexuality, the latter being standard procedure since I usually spent lunch period cowered over my tray while reading the latest edition of Metropolitan Home. By 2 p.m., my fedora had been stolen from my locker, a case worthy of a hard-boiled detective. But while Philip Marlowe would have roughed-up suspects and bantered with beautiful women, I marched down to the principal’s office to file a complaint. By the end of the school day, a janitor had located my fedora in a urinal in the boy’s locker room, its final resting place.

“You don’t want to be the guy in the fedora,” my friend Ken recently told me when I recounted my story and mentioned I was considering purchasing a new version of the hat. “When I see a guy in a fedora, I know he’s looking for attention,” Ken continued. “Don’t be that guy.” “But I’m fifty now,” I argued. “I’m at the age I can get away with certain affectations.” Ken checked his oversized smartphone then slid it into a plastic holster attached to his belt. “It doesn’t matter,” he said. “You’ll still look like a jerk.”

Unnerved by Ken’s proclamation, I decided to purchase a smaller fashion accessory, a silver signet ring with a face roughly the size of a fifty-cent piece. When it arrived, I wiggled it onto my middle finger and stood in front of the full-length mirror hanging in my bedroom. I jabbed my thumbs into the crease between my belt and jeans and tilted my head back and to the side. The light reflecting from the ring’s face was like a beam of masculinity. “Seriously?” was all my girlfriend Jess said when she walked by.

For the rest of the day I strutted around the house fueled by the confidence my ring conferred. I caught sight of its shimmering power as I folded laundry, sorted the recycling, and dusted the bookshelves. But when it was time to go out for the evening to meet a group of friends, I removed the ring and placed it in a tray on my dresser. As we walked to the car, I noticed Jess glance at my naked hand and smirk with an air of self-satisfaction. “Not ready to take the ring public?” she asked.

During the drive, I thought about my ring, and my ill-fated fedora, and that enormous chasm that lies between who I am and who I think I should be. I thought about all of the superfluous things I’d purchased over the years in a vain attempt to create a personal style: the French tote bag, the motorcycle jacket, the Italian handmade sneakers, items stashed in my closet that had never seen the light of day. I looked down at my navy t-shirt, my jeans, and my grey Adidas with holes in the soles. The uniform of a guy who can’t stand to look like he’s trying too hard.