The Perfect T-Shirt Sleeve Roll Is an Impossible Dream

It’s a fundamentally inexact science.

In life, some things are as ineffable as they are pleasurable: the fleeting prickle of the tips of a cat’s whiskers on your face as it pushes its head close to yours for an inquisitive sniff; the sharp tang of Pringles Sour Cream and Onion flavor when it first hits your tongue — so pungent it’s almost sweet; the weird chemical-y smell, somehow both clean and dirty, clinging to the pages of British tabloids. But this list, such as it is, would be lacking were I to overlook perhaps the most mysterious of these phenomena — the very particular James Dean-ian look of a rolled-up T-shirt sleeve.

The internet, predictably, is full of attempts to explain the unexplainable. How thin or thick should the rolls be? What height is right? And, maybe most crucially, how do the sleeves stay up? One site, after claiming that the look should appear “disheveled,” immediately gives this suggestion the lie by instructing its readers to “wrap an elastic band around the base of the unrolled sleeve” to keep it in place; a YouTube tutorial shows viewers how to use various other methods to secure the rolls, including a hair straightener and a safety pin; and GQ, by way of explanation, proffers a picture of the actor Justin Theroux on the street wearing a Boogie Down Productions T-shirt with its sleeves rolled up just so, and suggests that one should push the sleeves up until the shirt “looks like a tank top” and then flick them down with one’s palms so that they still turn up, just a touch.

GQ’s advice is probably the most doable and low-key of the bunch, and yet, there’s something about trying to come up with a how-to to break down and solve this puzzle that depresses me, that seems to me to defy the very essence of the rolled-up sleeve. As a generally uptight person, I revel in the opportunity the fairly limited arena of fashion affords me to at least pretend I don’t give a damn about how things look. Which is to say, while god knows I love Justin Theroux more than life itself, I can still sort of envision him secretly working a hair straightener on that T-shirt. I’d say that this doesn’t seem “manly” but that would be regressive, and also, the attitude I’m trying to get at here seems to apply to both men and women equally anyway.

What I like about rolling up the sleeves of my T-shirt in the summer months is the absentminded slackness of it. I roll them up quickly before I leave the house (no pins or irons or rubber bands — so not sexy), at which point they almost immediately start rolling down. Usually I end up with one sleeve up and one dragging, and by then I’m already out and sweaty, so I push the sleeves up over my shoulders, where they resume their slow, uneven descent, until the cycle is ready to begin anew. It’s a fundamentally inexact science — a platonic ideal I’m committed to pursuing while realizing full well it’ll never be reached. But then again, that’s kind of the point.

The Perfect T-Shirt Sleeve Roll Is an Impossible Dream