Prepare to Cringe: What 10 StyleCaster Staffers Wore to Prom

Leah Bourne
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When you’re at the tail end of high school, nothing comes close to rivaling the importance of prom. Looking back, it’s easy to see why: Not only is prom probably the first real formal event you attend without any adults that aren’t mom or dad, but it’s also a clear rite of passage that marks the end of something (your life as a boring teenager stuck at home) and the beginning of something else (the start of your new fabulous life as a seriously adult college student, or at least as a school-ruling high-school senior if junior proms were a thing in your town.)

Still, as crucial as it seemed at the time, let’s be honest: The whole thing is pretty laughable when you look back, from the gown you just had to have, to the limo, to your date, to the lined-up photos in your parents’ backyard. And don’t get us started on the corsages.

Given that it’s prom season around the country, we’re taking a look back at what we wore on the big night. Yeah, we’re going there—the good, the bad, and the downright hilarious fashion choices of our staffers—so buckle up.

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1. Samantha Lim, StyleCaster Creators Director 

When I was a senior in high school I went to the junior prom with a good friend of mine who was younger.  Since it wasn’t really “my prom” and I had spent most of my money on my own prom, I really tried to save money for this one. One shoulder dresses were very trendy at the time, as were glitter infused fabrics and ombre dyed bright colors. I bought this dress at DEB at the local mall for $69, my earrings and necklace were from Claire’s for probably $12.99, and since my date was pretty short, I wore flip-flops, in matching lavender of course, from Old Navy for $2. I think I did my own hair and makeup, because butterfly clips and glitter eyeliner were definitely involved. For an Indiana prom in 2002, I think I pretty much nailed it.

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2. Alle Connell, Senior Beauty Editor

I’m in the middle, with the tan and blonde curls, on my way to my high school boyfriend’s “Year 12 Ball” with his best friends and their dates. You’ll notice I’m wearing basically the same dress as the two other girls in this picture, which makes us look like a teenage wedding party. The dress I picked was the second dress I tried on, and I bought it immediately. I’d originally wanted something in pink or purple (the popular colors of the early 2000s), but I totally fell in love with this midnight blue silk dress. I glued silver rhinestones around the waist because I felt like it was a little bit plain, and I was really happy with that choice—I’ve always loved sparkle. I had been to three other proms (which were called balls in Western Australia, where I’m from) before this one, and I wore this dress to each of them. Every time, I felt like I stuck out—all the other girls wore very bright colors, and there I was in dark blue. In retrospect, I’m glad that I wore what I did because I don’t look back at the photos and cringe—until I see my pencil-thin brows, anyway.

MORE: 101 Prom Hairstyles You Need to See

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3. Samantha Skey, CRO

It must be said that the year was 1989. My dress was floral and above the knee and with two flouncy tiers.

Unknown-8 4. Ivy Davidoff, Account Executive 

I’ve always picked out all white everything—any piece of clothing my mother bought me, and if there was a color choice, I would pick white. My mom has always joked “You’re going to ruin your experience of wearing a white dress for your own wedding one day.” No surprise, when it came time to pick my prom dress, I, of course, chose white. Not only white, but a two piece set with some rhinestones on the top part. As we got into the limo, my friends kept saying “Mazel Tov” which is a Jewish phrase for congratulations and traditionally said at ones wedding. Based on the pictures, I can truly say that my white dress from prom is not going to spoil my joy in wearing white for my upcoming June wedding, and makes me even more excited to do it right this time around!

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5. Drew Tillman, Branded Content Senior Manager 

I opted for a masculine oversized rented tuxedo that gave me a perfect oblong silhouette. I carefully matched my boutineer to my dates lovely Tiffany green and gold dress. That night also happened to be a bad hair day, possibly the worst hair day of my life, so I decided to part my hair down the middle. Yikes, who does that? It truly was a tale as old as time

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6. Leah Bourne, Senior Editor

Let’s just say I was obsessed with finding the perfect prom dress. After buying at least a dozen with the plan to return them when I’d decided—from Lanvin to Gucci—I settled on a lingerie-inspired off-white silky Calvin Klein dress from the runway. I finished off my outfit with rhinestone-encrusted Manolo Blahnik gold sandals that cost more than shoes should ever cost, vintage rhinestone and pearl earrings that I found at a thrift store, and a gold lamé shawl that I had a tailor make for me (yes, it’s safe to say I was seriously indulged by my parents on this one).

Despite going to some pretty crazy lengths to have the perfect dress, my date showed up in a white tuxedo looking like he had stepped out of an old “Miami Vice” episode. Looking back, I think I must have been existing in some kind of delusional state that I was attending the Oscars, and not my dumb high school prom, but I still love my dress, and even wear it from time to time.

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7. Victoria Moorhouse, Associate Editor

I remember thinking that I just wanted to go for it for my senior prom—I didn’t care if my dress was long or short, but I wanted to wear something that I wouldn’t have another opportunity quite like prom to pull off. I tried on three relatively typical “prom dresses” but was really bored with them. Then I went into the Betsey Johnson store with my mom just to glance around, and ended up trying on a dress that made me feel like Barbie—hot pink, hearts, tulle, sequins, the works. It was so fun and not like me at all. I paired with it hot pink peep-toe heels I think I got at Macy’s, did my own makeup, and had someone curl my hair. I won’t ever wear that dress again (obviously), but it’s still in my closet.

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8. Rolando Robinson, Editorial Designer 

I went to prom twice in high school—my junior and senior years. At the time I was living in the middle of Tennessee (aka, “basic” hell), so it was even more important for me to dress outside of the prom norm—I wasn’t about to be caught dead at the same places my peers were getting their suits from. Junior year, I went with a friend who was a senior, and her dress was pink. I kept it classy wearing a grey Ralph Lauren suit and a metallic, petal pink tie, and white button-up shirt. Senior year I was a bit louder. Again, I wore a Ralph Lauren suit (but in black) with a black and white button up shirt, an iridescent teal tie, and Converse. My hair was much longer than it is now and straight, so I had a coif like you’d never seen before! Looking back, I forget who my date even was, but I know it didn’t matter because I ended up dancing with a boy anyway.

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9. Jasmine Garnsworthy, Editor

In Australia where I am from we don’t have prom, we have “formals,” but they’re basically the same thing—an excuse to wear a dress that cost more than my first car, and to get my makeup done. I had a dress made for my school formal, and picked a strapless, fishtail silhouette in white. Yes, I looked like a bride. Five years later I actually dug up that dress and found that despite the fact that it had been a half a decade since high school, it miraculously still fit (although it did have a red wine stain on it). I took it to a seamstress and had the dramatic fishtail hem cut off, and the dress was transformed into a cute white mini. I still wear it now!

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10. Rachel Adler, Beauty Director

For my junior prom I borrowed a dress from a friend (big spender!) but got my hair done at a salon into a very curled updo. I also clearly had a love affair with tanning beds at the time, and went with a shade of pastel purple shadow that would match my dress–not something I as a beauty editor would ever recommend doing today. For my senior prom, I honestly didn’t search that hard for a dress. I don’t remember where I ended up finding the one I chose, but I liked that it was a little different from the “gowns” everyone was wearing–it was strapless and simple (aside from the sparkly flower number on the side) and I believe cost $70. For some reason I decided to accessorize with white jewelry and dagger earrings, and I may or may not have been wearing a bump-it in my hair.

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