Overthinking Underdressing

Or is under-thinking overdressing?


Is it better to be overdressed or underdressed? I ask because I have historically empathized with she who hails from the latter group and as such, recently determined that the very question above informs more about my style than I may have initially believed it to.

I think I’m becoming casual-to-a-fault. My aesthetic leans more toward Narciso than it does Nike, and recently a close friend named Claire has been making the same joke, without fail, every time I walk into room where a celebratory, slightly-but-not-quite formal is being held: “Oh! Ripped jeans! For a change!”

You’d think the punchline would wear off after being repeated so many times but it doesn’t. This is probably because the only thing worse than a recurring joke is a recurring, out-of-place outfit.

At my cousins wedding the summer before last, I was almost asked to leave on the account of my pant-not-so-suit. For visual reference the pants in question were eggshell-colored charmeuse crepe palazzos; they hit the floor as spectacularly as they buttoned at my waist, and with them I wore a white silk t-shirt, gold choker and layered a light blue double breasted linen blazer over my shoulders.

“It’s black tie!,” my aunt yelled at me in her foreign accent. My mother, father, great aunt and a red headed girl I don’t know looked on while she assessed the visual damage I would inevitably cause to the bridal party, of which, mind you, I was not even a member. And to this day, every time I see that aunt, she reminds me that I wore pants to her daughter’s wedding.

Did I find it disrespectful? Absolutely not. Could I see where she was coming from? Indeed: Squareville, USA.

But more interesting than the actual clothes and the responses they continue to elicit is perhaps why I dress the way I do; why, when I see a pair of ripped jeans, the internal amicability alarm sets off and I am almost immediately wooed. Furthermore, no matter how beautiful the gown, how perfect the fit, how elegant I feel, I am never as comfortable when torn away from the clothes that make me, me.

This seems counterintuitive when considering the “identities” I so often speak of assuming via clothing (The Lady, or The French Girl, for example), but I’m going to trace this handicap back to a primitive, savage time: The Era of Bat Mitzvahs.

When one classmate of mine was turning her Holy Twelve, her parents threw a party at a JCC in New Jersey. These particular parties called for dresses, but style maverick that I was, I forewent the dress for a pair of green ill-fit trousers, a black shirt with white Mongolian faux fur trim and a pair of knee-high wedge boots that were a little small on me but still the most magical possession I owned, what with their leather leaves embroidered on the shoes’ calves.

It took my mom and me over an hour to get those boots on my feet. At the end I thought it was totally worth it, but when I got to the party, all the other kids were in t-shirts and jeans. This was a jungle gym party that had no place for embroidered leather. Nor did it for my hairpins. Everyone looked so comfortable and cool in their easy outfits that allowed for child’s play and here I was in itchy trim. I felt like such a fool.

So you know what I did? I disappeared into a corner to take off the shoes that stole an hour of my life and tucked the fur trim into my blouse while I wished I was in jeans.

Twelve years later I still can’t shake that night off. Why didn’t I just own how I looked? Why did it make me so uncomfortable? Is it possible that at just 12 years old, I’d already culled an idea about the implications tethered to being over vs. underdressed? Did I really know that to be the former meant you’d tried too hard and therefore to be the latter effectively made you Kate Moss — and effortlessly, at that?

I’m not quite sure. But it is possible that for everyone who’s tickled by getting overdressed or perhaps similarly, by looking like they don’t even know they’re dressed, a congruous story floats through their past. So maybe I’ll ask again — is it better to be overdressed or underdressed?

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