Friday night. New York City. You spent half of last month's paycheck on a new jacket that you've been looking at online for months. After three rounds of shirts, you're finally ready to go. You look great and you know it - nothing can stop you now. Fantasies of the night ahead race through your mind as you walk down the six flights of stairs from your apartment. Beautiful women, sure, but the way you look you are thinking beyond that. Someone might even mistake you for a king, you think, as you hop on your Citi Bike and head off into the sunset.
This is it. Your big moment, as you head out onto Sarah's rooftop you are ready for the applause or at the very least the compliments. However, right then and there, your acquaintance Jimmy, who has worn nothing but glorified sweatpants for the past 21 days yells, "don't you think you're a little overdressed for this?"
BAM. It all comes crashing down.
I'm sure you are all familiar with this exact situation. It's happened to the best of us. And, as with all good stories, it begs the question: is there such a thing as Overdressed?
"Well of course there is, Josh!" says the snarky reader. "Shut up, you know I'm not talking about wearing a tuxedo to a pool party" says the rambling, whining author.
In all seriousness, what happened to caring about how you looked? The days when matching watch and belt and a well ironed pair or pants were all you needed to see to know a man could be trusted. The days when you could walk into your office in a nice collared shirt, perhaps a turtleneck even, without a tech bro laughing at you while he drinks his sparkling green tea kombucha and consumes his entire daily nutrition in one 300ml bottle of sludge. White T-Shirt, Black T-Shirt, White T-Shirt, Black T-Shirt. It's enough to make anyone go insane.
Look, the point is this: caring about how you dress is cool. Getting dressed up is cool. That new jacket you got is cool. Most importantly, matching your belt to your watch and shoes is cool. And no, you can't be overdressed.