Round Table: Embarrassing Halloween Costumes We’ve Worn

Halloween is the best time for kids to try out all sorts of different looks under the guise of it being a costume. Here are some of our more unfortunate (yet unforgettable) Halloween costumes from our childhood!


Nina Fichera

From first grade to fifth grade, I was Stephanie from LazyTown. That wouldn’t be so bad, except my costume was completely home-made; I had a pink long-sleeve sweater dress, pink leggings, a pink headband, pink sneakers and a pink winter coat that my mom always made me wear over my costume so I wouldn’t get cold. The only part I bought specifically for the costume was a pink bob wig, which looked incredibly awful on me since my hair was already that short and couldn’t be pulled back for the wig. The highlight was in fifth grade when one of the moms at the costume parade recognized who I was! Nobody else ever did and I can’t blame them, haha.


Margaux Carmel

In seventh grade, I wore my first store-bought costume from Spirit Halloween! I was a “fallen angel” or something similar, but looking back at the costume it was extremely revealing for being a child’s costume. I wore it to school! I’m all for more revealing Halloween costumes for adults, but I’m not sure how that costume passed quality control… 


Nicole Kemmett

I can’t say I’ve had an embarrassing costume because I’ve loved them all, but I’ve been embarrassed about what happened in a costume. In my sophomore year of high school I went all out at the height of my history nerd phase and got a corset, overskirt, dress, flower crown, the whole nine-yards to be a medieval maiden, but I got my period that day and it was really hard to use the bathroom in a full corset. I got blood on my white skirt and ended up going to the art room to splatter red water colors over the skirt to look like a more murderous maiden and borrowed a friend’s fake blood to put on my face and look undead. Definitely my most impromptu costume shift. 


Emily Tsoi

I think I only wore store bought costumes like five times over the span of my 20 years worth of Halloweens. I’m not the most enthusiastic when it comes to Halloween. A lot of my costumes were just things I threw together at the last minute to resemble something, like in the fifth grade, I wore a tie dye shirt and called myself “a hippy.” The most embarrassing ensemble I threw together though was my freshman year of high school, I think. It was the one I called “chef” because I used things my uncle had given my dad, like an actual button-up shirt chefs wear and a chef’s hat. I can’t believe I actually went out wearing that because as I said, it was my uncle’s attire and so it was three sizes too large for me at the time. Yikes.


Monica Weber

Like Nicole, I’ve loved all of my costumes I’ve worn, so I can’t say that any of them were particularly embarrassing, but there was one thing that has stuck with me to this day. In elementary school, I dressed up as Gabriella Montez from High School Musical. This was in the peak popularity of that movie series, so I was extra excited to be my favorite character for Halloween. I remember going to school and when people saw my costume, they weren’t as impressed as I thought they would be. Instead, they informed me that Vanessa Hudgens’ naked pictures were on the internet. My elementary school costume was overshadowed by nudes leaking. Not fun. 


Lily Connerton

For most of my childhood and adolescence, I differed from my friends in choosing funny or scary costumes instead of the girlier/cuter options. (Does this make me a “bruh girl”?). Coupled with my enthusiasm for Halloween, this meant I went all out every year with fake blood, face paint, wigs and even facial hair. One year I dressed as simply ... a man. But it's none of these wacky costumes that stand out as the worst to me, since I felt confident in each of them and had fun planning and wearing them. For me, my worst halloween costume came the year I changed things up, donning a slutty policewoman costume from Spirit Halloween, complete with fishnet gloves and of course, handcuffs. As soon as I arrived at the bus stop, I immediately realized what a mistake it was, as a boy much older than me ever so kindly decided to nickname me the “prostitute police.” Yeah, I think I’ll stick with the ghost costumes. 


Mira Jaeger

Halloween has been my favorite holiday ever since I was about 4 years old, so I have a long history of very … enthusiastic Halloween costumes. When I was very little, I was set to go as a skeleton! I was so excited about it that I wore the costume everywhere. One afternoon, I fell asleep in it and woke up absolutely convinced I had turned into a skeleton. I refused to wear it again.


Julia Clancy

I would have to say my most embarrassing Halloween costume would have to be the Sharpay costume I wore for probably three years in a row. This was a personal choice, as Sharpay is one of the best characters in the HSM franchise, but the costume wasn’t exactly the most warm. Growing up in Western New York, more often than not Halloween was either really cold or really rainy. So, I had to wear my bedazzled skirt and shirt combo, and ratty blonde wig over my winter coat and thermal leggings. It wasn’t exactly the most accurate Sharpay costume on the streets, that's for sure. 


Dara Scolnick

I wore plenty of weird Halloween costumes growing up. In kindergarten, I was a bride. I wore what looked like a wedding dress. I don’t know why exactly, but I guess I really wanted to wear a white dress and veil. I also have always loved weddings so maybe that’s why. A couple of years later in elementary school I was a Bratz doll for a school Halloween event. I loved Bratz growing up. I think I was also a Barbie doll at some point. I didn’t even really like Barbie dolls; I think I just liked the outfit. I thought the costumes were cute so I definitely enjoyed wearing them for Halloween, but now I look back and can’t help but laugh at them.


Ally Schultz

Over the years, I have had plenty of questionable/embarrassing costumes. One of my favorites would have to be when I was around 5 years old. I called myself “a princess-fairy-godmother.” I could not make up my mind of which of those three things I wanted to be, so I decided to combine them all together. I wore a pink dress with a white long sleeve shirt and leggings underneath (thanks, mom), some glittery fairy wings, and of course, a tiara to complete the fit. Another year, I dressed up as a fisherman? I wore big boots, jeans, my dad’s vest that was essentially a dress on me and a hat. To top off the look, I wore a giant, long beard from one of my family member’s previous costumes. I was something, to say the least. 



What costumes have you worn?