I’ve spent the bulk of my adulthood in t-shirts. When I was a kid, my mom tried to keep me in polos (summer) and in rugby shirts (winter) so that I’d be a 10 percent more presentable child to the general public. Then I went to a prep school that had a dress code mandating that boys wear either a dress shirt and tie or a turtleneck, with me always opting for the latter and occasionally getting reprimanded by my teachers for trying to sneak mock turtlenecks into the rotation. But anytime I wasn’t obligated by my folks, or by some crusty old dean, to look “nice,” or at least the JCPenney version of nice, I fucking SPRINTED to the t-shirt drawer to get my identity back. And now that I’m a grownup who works from home, I can wear that identity at all times of day now. I am free.
But it turns out that looking free doesn’t always mean looking GOOD.
Like most everyone else, I’ve long made a considerable emotional investment in my t-shirt collection. I had a flag football championship shirt from my brief stint at Michigan that I wore like a trophy. I once had a New Kids On The Chopping Block t-shirt that I ordered from the back of Rolling Stone when I was 13, to let everyone at middle school know that boy bands were for wimps. I had a shitload of Metallica t-shirts—no boy band, they!—one of which was the same t-shirt Lars wears in the “One” video. I had a commemorative CBB championship shirt from my days playing D3 football. I had worn-out grays I stole from the prep school equipment room because they were great shirts and everyone stole them. And I had any number of generic graphic tees—from Old Navy and from a host of shitty oceanside surf shops—to let people know that I was the playful sort who likes being a walking, unpaid advertisement for Laguna Beach.
I wore all those shirts with both comfort and pride. And I’ve worn t-shirts to my home office so often that it was very hard, up until recently, for me to imagine wearing anything else while doing my dirty sinful blog business for you, the reader. Not only did I abhor formalwear, or even business casual, but I also looked awful in both. You’ve seen the gif. You have the receipt. More to the point, I have that American reflex where I treat any collar around my neck as a noose put there by THE MAN. Can’t hold me down with a tie, nossir. I yearned to be Maxin’ And Relaxin’ Drew at all times, clad in a t-shirt that let you know I’m not a tight-ass like all the office drones out there. I was cool.
I was not cool. I am not cool. I’m definitely not cool in a t-shirt. Look at any recent photo of me in one and I look like a dad lost at Disneyworld. All the vibes I imagined giving off in a t-shirt were nonexistent. I looked like a pud. And I wanna tell you that I deserve to look like that. But listen, I’m not a pud. I’m not a clueless asshole. I’m a goddamn professional. But I rarely, if ever, looked the part.
I had plenty of viable excuses for this. We just lived through a pandemic, so who was gonna see me look like a slob anyway? My kids? They didn’t care. My wife? Too late for her to kick me to the curb! Who was there to impress? I may as well be nude.
The other week I got a new polo shirt. Better polo shirt than the Chopped one. This one cost actual money. And when I put it on, I felt good. Great, even. I rifled through my closet for some old Uniqlo polos I never wore and tried them on, too. They also looked better on me than any of my t-shirts did. I know I clean up nice when the occasion calls for it. It’s only recently dawned on me that hey, maybe I would like myself better if I were cleaned up all the time. Without a special occasion to mandate it.
MILDLY cleaned up, I should note. My grandpa, who died a very long time ago, used to wear a coat and tie every day. Even to the pool. That befitted his standing as a family patriarch, and as an OSS veteran who went on to become a distinguished lawyer. But even though Grandpa was very much a product of his times, as we all are, he knew something that it took me far too long to understand: It’s worth looking good just for your own sake.
But I don’t think I can any longer. I probably haven’t been able to in a while. I’m not Harry Styles. I can’t use my God-given good looks to alchemize ordinary clothing into hot shit. Also, I pit out t-shirts in an instant, deodorant or no deodorant. I need assistance.
So, last week, I did an inventory of all my t-shirts. Half of them went to Goodwill, even concert merch I treated as sacred artifacts. The other half I relegated to workout duty. Then I went through my polos and discarded all the ones that made me look like a sixth grader. Then I took the nice polos I had left and put them where the t-shirts used to be, and that became my go-to shirt pile. I ordered more for that pile. They’re in the mail as we speak.
My wife noticed the difference. She was like, “Oh, that looks better,” and she’s not a woman who doles out cheap praise for cheap praise’s sake. More important, I looked good to ME. I finally felt the part. I wasn’t walking around my own house looking like a goddamn tourist at an airport gate, wearing a t-shirt that barely covers my dickdo and frumping my way from one Auntie Anne’s kiosk to the next.
Now, you’ve seen the Chopped polo so you’re already rolling your eyes and pantomiming jerking off at me for thinking—IMAGINING—that I look better than I have in the past. That’s all to be expected. You’re also probably gonna tell me I’m just wearing the WRONG t-shirts, and that I should invest in better quality ones. I’ve been there and done that. I even once had a v-neck from Armani Exchange. I tried wearing a sport coat over it a few times. I thought this t-shirt made me look like a baller, when the reality was that it made me look like Simon Cowell’s nephew. I have a body type, and no t-shirt is willing to flatter it. And no one is gonna give a fuck if it’s a vintage shirt from the 1988 Monsters of Rock tour, either. The time has come for me to try out life without one; to look in the mirror and feel like I look like the guy I’m supposed to be.
But you’ll take my hoodie collection from my cold dead hands.