But that, in the end, might be the biggest fantasy that attaches to clothes — namely, that any of us can ever have it figured out, arriving at a place of such self-knowledge that we no longer err. The way you look in clothes is, in fact, a profoundly flawed and paradoxical marker of self-knowledge, because the way you look in clothes is, ultimately, not just up to you. It’s up to other people. What’s more, as with any social compact, it’s subject to an endlessly shifting, inescapable array of historical contingencies and aesthetic renegotiations — or, as we familiarly describe them, trends.
That’s why David Lynch has never found his perfect pair of pants. Because David Lynch’s perfect pants, much like David Lynch’s perfect self, do not and cannot exist. That impossibility could drive us nuts, or we could embrace it — take it as a license to play around with how we see ourselves, to keep testing the borders of our comfort zones, trying on different selves, one pair of pants at a time. In this light, Noah Garfinkel’s joke about how “you should always be wearing pants you think look stupid” might contain some of the wisest style advice I’ve encountered: Your capacity for stupidity is how you know you’re still alive.
Recently, a late-period portrait of Miles Davis — as universal an avatar of coolness as modernity has produced — made the rounds on style-focused corners of the internet. This was not the natty, circa-1950s, Oxford-button-up-and-slim-trousers Miles Davis we’re used to seeing. He has long hair and tiny sunglasses. He is leaning against a white Ferrari Testarossa. His name is on the license plate. But none of that is the focal point. The focal point is Davis’s enormous pants. They are tan, with deep pleats and a towering rise, and they pool behind the tongues of his white loafers like tidal waves converging on a couple of dinghies. They are large but not structureless — they echo and expand on his stance with a graceful excess, the way a sail echoes and expands on the wind. They look tremendously, gorgeously, inspiringly stupid.
I think there’s a lesson in this picture for those of us who wear pants — even the 100 percent of us who are not Miles Davis. As I write this paragraph, I’m sitting in a pair of wide-legged, double-pleated, dusty-eggplant-colored corduroys. When I glance down at them, they feel stupid to me in the most pleasingly strange, personally appropriate way possible. When I get up and walk around, the way they slosh around my legs strikes me as even stupider. I love them. Maybe the best I can do is hope that my pants feel like this for a very long time — and that if the day comes when they don’t, that I’m not too tired, or too proud, to find another pair of pants this stupid.
Stylist: Karolyn Pho. Groomer: David Searle. Makeup: Sara Tagaloa.
Jonah Weiner is a contributing writer based in Oakland, Calif. He writes Blackbird Spyplane, a style and culture newsletter, with Erin Wylie.
