Wear an Ugly Prom Dress

Three hideous (but ideal) prom dresses from Never Been Kissed, 10 Things I Hate About You, and Pretty in Pink.
Three hideous (but ideal) prom dresses from Never Been Kissed, 10 Things I Hate About You, and Pretty in Pink.

Welcome to Teen Week!

The outfit I wore to my junior prom was very tasteful: a black tea-length cocktail dress that—still hanging in my closet back home—looks as appropriate now as it did in 2004.


At the time, I was worried about how the photos of me going to prom would age. I’d seen photos of proms from the 1980s—big shoulders, ruffles everywhere—and wanted to avoid that, so I relied on the look of old Hollywood, pairing my dress with a single orchid for my hair and sparkle of costume jewelry. It was very affordable and very, very boring.

To this day, I believe that prom should be a budgeted experience because it teaches you the value of LOWERED EXPECTATIONS. That said, if I could do it all over again, I would have worn the most hideously trendy prom dress of all time.

Prom dresses shouldn’t be timeless, they should be tragically of their era. Ultimately, prom is just a chance for teenagers to act more sophisticated than they are by dressing fancy, eating at nice restaurants, and, if you’re like me, feeling wracked with guilt because you had a harmless no-touching fast dance with a friend’s boyfriend and you think she hates you now (she doesn’t). Everything is silly and over the top and your outfit ought to reflect that with sequins, ruffles, or whatever else is “in” now and won’t be in later. Looking back at your prom photos, it it’s both a duty and honor to cringe in embarrassment because that’s what’s fun about remembering your generation’s prom.

While I was (mostly) dancing alone in my timeless dress, I was surrounded by classmates with up-dos so shellacked in hairspray that they could safely ride a bike without a helmet. There were students in puffy skirts and and poorly fitted princess bodices, two guys showed up in the tuxedos from Dumb and Dumber, and, in a similar vein, a fellow classmate showed up looking adorably ridiculous in a replica of the dress Kate Hudson wears in How to Lose a Guy in 10 Days. Better still, she was on prom court, so the photos of her—a baby-faced teen strapped into a synthetic version of a dress designed for Kate Hudson at her thinnest—are ample.

Do you think she regrets it? I highly doubt it. At the time, I bet she thought she looked banging and now, at worst, she looks back on that outfit and is, at the very least, charmed. I know I am.

When I think back to prom, my memories are mostly underwhelming, but what I do remember—and remember fondly—are the more awkward moments of the night. None of my friends had dates so I drove everyone there (there being the basement of the masonic temple where our prom was being held) in my mom’s minivan. We listened to Rent on the way. Later that night, I got drunk for the first time and spent the rest of the evening horking up the fancy dinner I had saved up for in the bathroom at a house party before crawling off to sleep in a bunkbed, only to be interrupted by a couple who came in to fool around on the bottom bunk not realizing I was in the bunk above.


It was a ridiculous and disappointing at the time, but in retrospect, it’s the messiness that makes the night remotely memorable. Sure, I was able to dry clean the regurgitated fried chicken out of my boring black cocktail dress so that I was able to wear it again, but, SNORE, who cares! Tasteful cocktail dresses are a dime a goddamn dozen, whereas you only have a chance to wear a hideous trendy prom dress one-to-three times in your life (maybe more if you either failed a couple grades or creepily continue to date high schoolers after graduating).

You’ll never fully be able to revisit the feeling you experience during prom itself (if for some reason you want to get close, drink some warm peach schnapps and grind to “I Don’t Wanna Know” with some guy with a half chub), but you can at least look back and know you did it right—by wearing an ugly-ass dress and (safely/harmlessly) making a fool of yourself—the first time.

Managing Editor, Jezebel


Montauk Monster

I wore a red-and-black (satin?) tartan ballgown to prom. It was basically this (not me) without the straps & petticoat. No, I am not Scottish. Yes, I was medium-goth.