In early September of 1992, I attended a new student orientation at an upscale middle school in West Hartford, CT. I was entering the 6th grade and transitioning from life in Washington, D.C., with all its go-go music and generally lackadaisical attitudes to style, to life in suburban New England. I, along with a handful of other new recruits, was seated in a semi-circle facing the institution's dean of students (upscale middle schools in Connecticut have these) when he delivered a crucial blow. We were subject to a strict dress code.

My peers smiled and nodded. They were all clad in their parents' vision of Ralph Lipschitz's dream. Against the assembled polos and pressed khakis, I stood out in my Eastern Tennessee State University T-shirt, Levi's and a take down version of the Nike Tech Challenge II. The dean was clear in his articulation of the code: While the others were teetering on success, I was in clear violation. "Do not dress like that," he said, pointing at me.

Officially, sixth graders were in the "upper school," which meant that we were required to wear blazers, shirts and ties or, alternatively, a sweater and a turtleneck (why this was an appropriate option still puzzles me). No jeans. No sneakers. We were told that "this is how you dress for work!" It was expressed that as students, we were professionals. The way we looked signaled the beginning of a successful, fruitful adult life.

We were shackled by tradition—blue blazers, red ties, Weejuns. For the first time in my life, I faced the frightening specter of homogeneity. To make matters worse, I also confronted the ugly realities of classism.

"We have to wear ties," explained one misguided science teacher, "because white men rule the world, and need to feel some discomfort."

Dreams held by other students included admittance to Deerfield, four years at Colby, law or medical school and ownership of a Ferrari. In short, the typical dreams of the comfortable white man. One friend, after receiving a C on a math test in the 7th grade, cried openly and exclaimed, "I will never become a doctor now." It was equal parts comical and sad.

While most other students conformed, I sought ways to stress the boundaries of the rules. Gramicci pants—those gusset-crotched climbing trousers—didn't have a fixed waist, but certainly couldn't be classified as jeans. I realized that if I wore a sweater with a turtleneck, there was no arguing that I need two garments to complete my outfit. I also discovered a truth held dear by aging preps: Hiking boots, when brown, will not draw the ire of the decorum gods.

The dress code revealed something important: The types of kids who wanted to become doctors and lawyers were FUCKING LAME.

On rare occasion, we were allowed to dress down. Lacrosse shorts were king, as were hand-me-down Phish tees. Big Johnson T-shirts, incendiary as they were, were banned. I recall wearing a royal blue longsleeve T-shirt, authentic home North Carolina Tarheels hoops shorts and Nike Air Lambastes. I also, embarrassingly, remember wearing a massive pair of baby blue sweats and a Public Enemy sweatshirt. I wore anything to signal that my interests were completely divorced from those of the type of people who loved Blind Melon and the Spin Doctors.

The dress code revealed something important: The types of kids who wanted to become doctors and lawyers were FUCKING LAME. I wanted to be like Shaun Palmer, a pro snowboarder who was covered in cool tattoos, essentially a white version of 2Pac. He, and others, revealed an alternative based not on abstract rebellion, but actual reality. In other words, unlike my misguided science teacher, Shaun Palmer suggested that you could simply wear whatever the fuck you liked to work. And, if you chose the right profession, be quite successful in doing so.

Those middle school years also functioned to sour my future. When I became a museum curator after graduate school, all was great except the fact that I was forced to dress like the bizzaro douchebag version of 12-year-old me. Blazers and ties, again the norm, precipitated a spiral into deep depression—not just sartorially, but mentally. Thanks to 1992-1995, traditional menswear simply crushes my spirit.

I'm not immune to rules. Weddings, funerals, etc. all deserve standard, regulated dress. However, those moments are infrequent and, though plagued by societal constructions, do not reek of attempts to standardize lifestyle. Now, when I walk to work (occupying a strange middle management position here at Complex), I often dress like the kid once used as a poster boy for failure to comply. I do so with a certain level of satisfaction, knowing that sacrificing individuality does not indeed correlate to sacrificing opportunity.