A guy walks into a bar wearing a crisp shirt when everyone else is in tees. That dinner you didn't bother to change for ends up being classier than expected. If you're famous, whatever, you can get away with anything. For the rest of us unwashed mortals, overdressing and underdressing are real problems.
I never worry about wearing a tuxedo out to walk the dog or showing up at the opera in a stained hoodie. Those are in the same category as dreams about showing up naked, which belong only to people who secretly want a pants-less workplace or are actually worried they might just forget to put on clothes. Over and underdressing are almost always in the details. The rest of the world might not consciously process them or even notice at all. But how we dress is how we act and they definitely will pick up on that.
I go back and forth on which one is worse, over or under. Overdressing says you're preening and way too eager, which is admirable, but also lame as hell. Clothes should be felt and not seen. If they're not coming off as effortless then you're trying too hard. That gets in your head. You start to wonder if everyone else sees it too and then you've got no choice but to run into the bathroom to cry it out or spend the whole night feeling self-conscious. Maybe I should change all these "you's" to "I's" because this is the part where someone invariably says, "You don't live in New York, do you?" Other than Long Island, I've never even been there.
But there's some gray area with overdressing. For one, it's way easier to remedy. Roll up your sleeves, lose some buttons, mess with your cuffs, take off a layer. Or just slouch around like you're trying to squander whatever outfit glory you've managed to achieve. Nothing fixes overdressing faster than convincing the entire room that you got dressed by complete accident.
If you're incapable of reaching out to other people and, instead, treat every day like a lookbook shoot, then you become irrelevant and maybe even invisible.
Practically speaking, underdressing is a far bigger problem, which might be why you have to either admit total defeat and accept inferiority or own the damn thing. Sleeves can't grow. Buttoning your collar might not be your thing. Wrecked jeans aren't magically healing themselves like Wolverine. Sneakers are sneakers and if they're beat up, you probably aren't going to duck out to clean them. You've got to let it turn you into an asshole in a good way, where you pretend you're rich and famous and that nothing can touch you. You've got to embrace the FUCK THE WORLD petulance of being underdressed and, for most of us, resenting everything around us is easier than resenting ourselves. Also, in some weird way, being underdressed also makes you the underdog, as opposed to overdressed, which makes you that guy who tries to up the ante for everyone else.
I know, I'm making a lot of assumptions about what passes for dignity. Shouldn't we be subverting formal/informal and making stuffy spaces recognize the strength of true style? I guess you're all way more confident than me or pretty oblivious. I guarantee you there's going to be a moment in your life where you suddenly feel very small, young and clueless. No one is made of iron. You can tell yourself that the world doesn't revolve around you and that nobody really cares what you wear. Except, on the surface level, they do. And a lot of the time, it's not about what people are thinking about you, it's what you think they're thinking and what you think about yourself. There are devils inside us all.
I don't mean to suggest that conformity is a virtue. Overdressing and underdressing are subjective, relative, situational, contextual, personal and any other word I can throw out there to make the point that there are no absolutes here. But if you never feel like you've gone too far (or not far enough) then you've got no range and no sensitivity to the world outside yourself. I'd even say that if you don't know how to dress for settings or people or places, you're missing out on the part where clothes are about more than just you.
Fashion should be social. If you're incapable of reaching out to other people and, instead, treat every day like a lookbook shoot, then you become irrelevant and maybe even invisible. Stunt away and fuck up the game as much as you want. At the end of the day, if you never overdress or underdress—if you don't take that risk—you might as well spend all day just looking in the mirror.
Bethlehem Shoals is a writer living in Portland. You can follow him on Twitter here.