For a Fashion Dirtbag, the Element of Surprise Is Your Greatest Ally

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Photo: Getty Images

Every night before I go to sleep, I lie flat on the ground and say a little prayer. It goes something like this:

To the holy goddess who blesses my day
Please no more wedding invitations until at least next year
Thank you

Weddings, like sports games, are generally fun. There is food, alcohol, partying, dancing, throwing up if you play your cards right, kissing, the Cha Cha Slide. You know the deal. You’ve all been to them, or at least seen them on episodes of Friends. But the difference between a wedding and a sports game is that at the latter you can dress like you have just woken up from a three-year coma and at the former you have to look presentable. This is a challenge for the person who is a dedicated fan of the T-shirt, generally prefers cheap clothing, and has put off figuring out the line between looking acceptable and looking nice for as long as they’ve been on goddess’s green earth.

To my fellow dirtbags who are about to attend a wedding or an otherwise “fancy-dress event,” here’s a nugget of advice: The element of surprise is your best friend.

As I’ve mentioned before, my closet contains several ugly dresses, several ugly blouses, and a few ugly skirts, most of which I’ve anti-Kondo’ed and held on to for several years despite the fact that they bring me absolutely no joy. But the reason they bring me no joy isn’t because they’re necessarily unwearable, it’s because the thought of wearing nice attire and “fancy dress” makes me uncomfortable. Ah, fack, I think. Another terrible event at which I have to pretend that this zipper is not digging into my side and the strapless bra that I spent 60 dollars on isn’t making me feel like I’m flashing the bride’s cousin. These are not the proper circumstances under which to do the Cha Cha Slide. At the last wedding I attended, I almost resorted to wearing a navy-blue sack, but at the last minute I gave in to something more fitted. I’m weak.

Some people love putting on a pretty dress or a pair of clean, pressed slacks. These people say a different prayer at night, asking the holy goddess for more wedding invitations so they can acquire more Rent the Runway floral gowns and elegant sheaths. These people are insane. Why? Because when you are a person who dresses up regularly, a person who has an entire array of clean and nice outfits at your disposal for any number of exciting events, you are given fewer compliments. You dressing up again? Old news. And that is why the element of surprise is so important.

When you are inclined to dress casually, the few times a year that you deign to dress up (even if at a wedding or more spontaneously, like at the DMV) will begin to feel like those scenes in teen films when the nerd takes her glasses off. Oh, damn, everyone will whisper among each other. She really does clean up nice. She must choose to not dress so formally all the time because she has better things to worry about, like thermodynamics or solving world poverty.

Every so often, to throw off my colleagues, I will come into work wearing one of the dresses that I own, sometimes paired with (fashion term) a red lip (beauty term) and some chic heels. You should see the faces of the people I encounter throughout my day. Often these people ask me, “Are you going on a job interview?” or “Were you on TV this morning?” Once, I was going on TV that morning, but I lied and said no. Why? Because people need to know that at any given moment, I could show up at a black-tie gala unannounced and blend in like the scammer I am. Until then, I plan on capitalizing on those moments for the heaps of undeserved praise. There is nothing more important in life than keeping everyone in your orbit on their toes. In the end, you, the humble dirtbag, are the hero.

And if you don’t believe me: Just look at men. This is what they’ve been doing since the dawn of time.