THE RALPH LAUREN AGE: When I started college, I still had little idea of what constituted acceptable fashion, but at the age of eighteen—far later than some of my more astute, non-cargo-jort-wearing classmates—I finally started to realize that clothes weren’t just functional. In fact, clothes were the opposite of functional. They existed only to make you uncomfortable and to signal to the world that you had money or taste, or that you cared enough to make people think you had either. Oblivious to fashion beyond what I saw directly before me, I did the best I could and mimicked college bro culture: I replaced all of my T-shirts with Ralph Lauren polos, my cargo jorts with pocketless khaki shorts, and my raggedy sneakers with boat shoes. I’m not proud of this time in my life. Mostly because it was the first time I had to take full ownership and responsibility for what I put on my body. Honestly, if I had come across me in 2008, I would’ve happily drowned myself in a lake and left the boat shoes to drift away as a symbol of the sins I committed that year. It was a dark time.

THE PURPLE UNDERWEAR AGE: When I finally came out in my later college years, I hadn’t brought any fashion knowledge out with me. But I was determined to show my pride in my own little way. I was interning in Chicago, and on my lunch break, I would wander over to Macy’s and browse the underwear aisle, finally deciding to buy a flashy pair of purple undies with white trim that cost me something like fifty dollars because for some reason, something that grazes your butthole all day costs an entire fifty dollars when it’s a fancy color. But I was a newly minted gay, and owning a pair of purple underwear felt like an appropriate first step toward my new life as a homosexual. Of course, the underwear didn’t come close to fitting my enormous thighs; it was like trying to fit a rubber band around a pork roast. But still, that underwear represented my new foray into the fashion world, one where I made choices for me, even if they cut off all circulation to my lower extremities.

THE PLAID AGE: You would think I’d feel pressure, living in New York City, to care more about my fashion choices, but honestly, I feel like I’m doing everybody here a favor. How else would you spot the GQ models of the world if you didn’t have a mangy schlub like me to compare them to? You’re welcome, David Beckham. Without me, nobody would know how hot and well dressed you are. And I’m perfectly fine with that. Because I don’t really have to look at me.