A men’s store in the Westport district of Kansas City—the closest thing we had to a “hip” neighborhood when I was in my late teens—was going out of business. Everything had to go—even the leather pants.

I wasn’t quite sure what to think about leather pants. I knew that they had a long history on the legs of rock stars and West Coast survival types who only washed themselves when it rained, but I was going through a period of fashion experimentation and thought I might be able to kick-start a local trend. (Much like I had done in middle school, when my pin-striped engineer’s overalls precipitated a hip-hop-inspired overalls resurgence, although I only wore mine fashionably half-clasped while receiving after-school beatings. The leather medallion embossed with a map of Europe I’d made in shop class probably didn’t help.)

The leather pants I selected were made from several smaller flaps of leather sewn together, which in retrospect should have been a warning sign. (Other warning signs: the billowing, Hammer-don’t-hurt-’em cut; that the store going out of business.) They weren’t cheap at $60, a princessly sum for me at the time, but they’d been over twice that new, and I was sure that my moment to secure a pair was then or at some unforeseeable point in the future while I was fronting a successful rock band.

I didn’t even try them on in the store, too embarrassed to try them behind the thin curtain of the store’s dressing room. I brought them home and tried them on in my bedroom, that familiar cold knot expanding in my guts as I realized I had no idea what proper leather pants were supposed to look like and no idea what sort of shirt should go with them. After several minutes of fretting, I put them back in their bag and went into the kitchen to cook some ramen.

It’s not uncommon for me to purchase some risky piece of clothing, be stricken with fear and regret, and file it away for a emotionally brighter day. (It’s not a bad system. I’ve saved myself from some embarrassing mistakes or let pieces “cure” until I could understand the context in which they should be used.) The leather pants sat in their bag on the top shelf of the closet for several months; every time I tried them on again, the flapping expanse of thin, stitched material over the back of the thighs and knees made it impossible to pair it with a shirt, let alone shoes.

One day my friend Chris came over with his new girlfriend, a sweet if slightly daft girl he’d met while studying to be a nurse at MU. She was the kind of girl who was enchanted by the drug-fueled boredom of our alterna-tot scene by proxy. You could tell she thought the artists and musicians of our burnout scene were exotic; I could tell she was a sweet girl with a sweet ass. (Chris always had a penchant for dating sane, sweet girls, a lesson I should have picked up from him sooner.)

Chris suggested we go to Cool Crest, our local mini-golf complex that happened to have the best arcade around. Inspired by his new girlfriend’s doe-eyed titillation at hanging out with a real live drug addict, I knew that I had to give her a good show, if only to make sure that Chris could fully exploit the “I have weird friends” card. It was a day for leather pants.

I remember the look on her face when I stepped out of my bedroom, something between the shock of wetting oneself and seeing a BMX kid lose his bike at the apex of his jump. She was too innocent to be entirely sure that I was out of fashion. There was the glimmer of possibility that I was at the cusp of a new trend. Her hope steeled my own.

Off we went to Cool Crest, where the green turf of the links would serve as my catwalk.

It’s not like the Independence kids that loitered in the ambient bleeps-and-meth haze of Cool Crest were the best candidates for my style quorum, but I’d unwittingly drafted them into service when I walked in the door and sauntered confidently to the change machine. As much as is possible in an arcade, the room went still. My confidence puddled. No eye contact was made. I went to the Silent Scope sniper game and slipped in my quarters with sweaty fingers.

My face planted against the plastic ring of the full-sized gun scope, I didn’t immediately notice the slow detour of kids around my machine. They’d end their circuit at the air hockey table, pooling into a group soon large enough to begin heckling. All told it wasn’t the most traumatic event in my life—I’ve been called a faggot by better—but it was soul-crushing to be shamed out of an arcade by 14-year-olds, especially in the company of Chris and his now pink-faced girlfriend, who joined me as we made a quick escape to the parking lot, a couple of especially hateful kids in tow.

It wasn’t a total loss. I learned that when I get that pit-in-the-gut feeling, it doesn’t mean that my outfit is awful or great. It simply means I’m stepping outside of my comfort zone—time to surround myself in a temporary shield of irrational confidence and a willingness to be shamed in public by teenagers! In the grand scheme of things a little humiliation is a small price to pay to expand your wardrobe choices, not to mention the self-confidence needed to really sell the ballsy outfits. (Chris’s girlfriend even took to pleasantly mothering me instead of shunning me forever.)

I never wore the leather pants again. I think I gave them away to my old roommate Lennie, who—god bless him—would wear anything.