The Hunt Begins…

“Why are you wearing that?” This question was posed to me by my then-girlfriend-now-wife the summer after we started dating. The question sounded odd to me, like someone asking why are bricks hard or why is whistling annoying. I had honestly never thought about it.

Growing up as the youngest of three brothers, I really didn’t have to. If anyone had asked me, the answer would have always been, “because this is what my brothers used to wear, but now they don’t because it doesn’t fit them anymore. So now it’s what I wear because it doesn’t fit me yet but I’ll grow into it, I’ve been informed.” There’s photographic evidence of this cycle of supply and recommended-demand: a picture of me wearing a shirt so large that it could, at first glance, be mistaken for a flag flown at a baseball stadium.

Eventually, the fountain of older brother clothes dried up, and I had to start buying my own–the rude awakening of many post-college humans. But I was a human with a bachelor’s degree and a solidly well-rounded liberal arts education; I was going to approach this clothes issue with logic and sagacity. Previously, the way I knew that I needed new clothes was that one of my parents said, “your brother doesn’t wear this shirt anymore, and your other brother doesn’t either, so you could use a new shirt.” Now I had to develop my own criteria for when the bell would toll new clothes o’clock. And in true college student spirit, I decided the easiest way was the correct one: I would get new clothes when it was physically impossible to wear the old ones. So, if I accidentally sat in between two couch cushions and split a pair of boxes in half–time for some new boxers. But, if the collar of a shirt is covered in a ring of sweat stains–hmm, we’ll have to form an independent fact-finding committee to evaluate that. Spoiler alert: the committee’s findings were inconclusive, and the fashion judge ruled that in the absence of concrete evidence, the shirt is wearable until proven filthy.

Which brings us back to my girlfriend’s query. The “that” in question which I was wearing was a pair of shorts that were wardrobe veterans of mine since my freshman year of college. As such, they bore marks on them that could be the apparel equivalent of a purple heart. They were also so wide that my legs were probably in there somewhere, but it was equally as plausible that I was wearing two black holes that were sucking all leg-related matter into an unknowable abyss.


Her next statement was as mind-blowing as her question: “You need to update your wardrobe.” Clothes could be updated? Not just replaced? Scandal! Outrage! Genius!

This led to a host of other revelations like: “It’s possible to pay an extra dollar or two and in return receive anything other than Bud Light,” “Hey, wine’s not bad either,” “Buying effective skincare products really makes your skin look like not-garbage,” and “well-prepared food tastes nice.”

And so began my journey to explore how looking decent and being classy was maybe an okay idea. This blog will be a catalog of my stops on that journey. Hopefully it will be an insightful, funny, and enjoyable look into becoming a (somewhat) classy man.