Parading around my apartment in my recently-purchased black beaded jumpsuit--vintage, naturally--I pondered how best to style it for a work event. Was it really worth sacrificing the integrity of the garment by hacking out the sizable shoulder pads? Which shoes would be a better match; the champagne glitter pumps with pom-pom ankle straps, or the pink suede ones with a reflective heel?
I live by a very simple maxim: Dress to regret. Not in the moment, of course. Always wear clothes you like. I’m also not advocating for dressing like a mid-2000’s C-level celebrity (looking at you, Bret Michaels), or for propping up the environmentally-destructive fast fashion industry (a la Primark or Forever 21). Rather, I view fashion as a way to take risks in an otherwise hyper-structured world.
To understand this motto, let’s take a look at my calendar. I have three internships, one part-time retail job, and I’m finishing my fiction thesis. For each of my jobs, I must comport my behavior to the standards of that workplace. No matter what I might think about a contributor or donor, I must retain an appearance of relative placidity. As anyone who has ever had a job can attest, I cannot fully be myself while at work.
Luckily, all workplaces have relatively lax dress codes, and I take every opportunity to exploit that leniency. Velvet platform sneakers? Absolutely. Gold mesh bomber jacket? Sign me up. Though I know that one day I’ll fish these garments out of the depths of my closet with a look of horror, today, it’s easier to express myself with my wardrobe than my voice.
Unusual clothes have yielded real differences in the way I’m treated. The dating strategy of peacocking might be ridiculous, but the theory behind it is sound: a memorable outfit is one of the easiest ways to spark up a conversation with a stranger. One of my first non-work conversations with my manager was about her hot pink Swedish Hasbeens, a shoe I envied but didn’t know how to style. Her advice was sound: “I don’t know, I just put them on.”
Regrettable clothes are an easy step for introverts and the socially anxious to open themselves to new experiences without doing too much. It’s not so much a confidence boost as it is an abandonment of concerns. If I could put on this ridiculous artichoke-print dress, why can’t I speak up in class? It’s a lot less embarrassing than what I’m wearing.
Sure, I might look back at old photos and cackle at what I wore way back when. But dressing to regret helps me live in the moment. It helps to turn my affected nonchalance into an actual sense of confidence. I might even say something like YOLO if I didn’t still have a modicum of shame.
My style has gone through phases. In middle school, I wore skirts over jeans because I idolized Juno MacGuff. When I lived in Manhattan during my freshman year, I wore lots of scarves because I yearned to be a Fashion Bitch™. Most recently, I wore a floor-length floral gown while visiting Versailles because I wanted to feel like a queen. While none of these outfits are particularly similar, they all have one thing in common: I was feeling my look. Every outfit we wear will at some point seem ridiculous. But rather than looking to the future and thinking of our closets for posterity’s sake, all we can do is lay out our wardrobe and wear what stands out to us today. Make an outfit worth regretting, no matter what that means.