Senior Producer: Kiran Chitanvis, Camera Op: CJ Dominguez, Creative Producer: Joon Chung

Shirts: My friends, they are a fact of life. I long ago realized that, with the exception of some jobs for which I am not remotely qualified, having a job would mean wearing a shirt of some kind, quite possibly to an office. At least partially as a result, I went on to freelance for the better part of a decade. I was not generally shirtless during that period, but that avenue was open to me.

At some point, though, things had to change. Freelancing melted my brain and led to a lifestyle that was nonsensical and extreme in ways that somehow managed to be neither fun nor cool. Imagine Ray Liotta melting down and ducking helicopters near the end of Goodfellas, only instead of clammy Ray being coked into paranoid psychosis and Dropping Off Some Guns At Jimmy’s it’s me wearing shorts and sending out emails all the time and spending all day sitting in weird positions on a futon. The situation was no longer viable. And so, later in life than is frankly excusable, I started buying proper shirts, of the kind that people wear to work, so that I could wear them to work.

It turned out that I have a type or two of shirts that I like, and it also turned out that the Goodwill (and, to a lesser extent, the fancier Housing Works) near where I live have a lot of these shirts. They are the shirts that uncle-grade normies like myself like, and I am happy to be the second person to own these items given that, when purchased that way, these shirts cost roughly as much as a decent beer. There is also dormant in my brain the tragic record-shopper impulse, which means that the process of browsing through a bunch of dusty useless things in search of a dusty useful thing is like a drug to me. (It is also true that a big part of why I go to Goodwill is to look for the bizarre and unexpected NBA jersey flotsam that often washes ashore there.)

But I don’t really wear those jerseys outside my home or even really at times other than when I’m cooking, and it is also true that I like my near-identical Blogger Dipshit shirts. I like having them and I like wearing them.

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In the video above, I unpack both my closet and my process and lay out a list of practical best practices for those aspiring to join the shirted community. Also I stand in some strange ways, look kind of jowlier than I’d hoped, and shaded what I intended to be a subtle Steve Brule homage into something a lot more overt. My hope is that you find it useful. My suspicion, which is stronger, is that there’s something wronger with me than I know.