Do you have a favorite school photo? We asked this question on Instagram and oh. my. gosh. did people deliver. Here, 11 Cup of Jo readers share their school portraits and the feel-good stories behind them…
Above: “My kindergarten photo makes me laugh because my mom bought a uniform that was three sizes too big so it would ‘last.’ I ended up wearing it well into elementary school.” — Maddie, New York
“Here I’m in the third grade, and the sports background was very much a ‘I swear I am not gay please no one find out I am gay’ trying to fly under the radar moment. That tie was my FAVORITE, and I wore it every day. I went to a Catholic school, where ties were the only form of self expression we had.” — Dan, New York
“I love my seventh-grade photo. It was right before I hit puberty, and there’s still so much ‘girl’ in me. My eyebrows are still intact, before I overplucked them the next year, after I got my braces off and felt hot.” — Erin, North Carolina
“In fourth grade, I thought I resembled Jennifer Aniston, and my parents never told me otherwise. My hair, my smize, my Limited Too shirt — I had no idea how awkward I was. Now I hope to impart the same confidence in my daughter that my parents instilled in me.” — Sari, Illinois
“In 11th grade, I was a springboard diver, class vice president, and member of the art club, AND I went to Lilith Fair. I peaked in high school. Everyone’s worst fear. Hahaha.” — Sharon, Connecticut

“When I was in third grade, my uncle went to Paris and brought me back a beret. It immediately became my entire personality. I was a budding theater kid with big feelings, and I told my mom that I’d be wearing the beret in my school picture. God bless her for not turning it into a fight. She always encouraged me to be exactly who I am.” — Katy, New Jersey
“For my second grade photo, my mom let me wear dangling Mexican hoops for the first time. That was the day my love for wearing hoops began.” — Lisa (left), California
“In sixth grade, this was my face after the photographer said, ‘Say BOYS!’ Maybe I would have given a big smile for ‘puppies,’ but not boys!” — Katherine, Georgia
“The year is 1987. I’m in seventh grade, and nobody has figured out that I have naturally curly hair, so my mom gives me a HOME PERM to try to tame my mane. Despite how cringey this photo is, I still see myself today, the optimistic dreamer who’s always quick to smile.” — Tammy, Ontario
“I call my first-grade photo my Ramona the Pest look! Now, as a middle school teacher, I share my school photos with my students so they can see that we all had our awkward stages.” — Martha, Washington

“Someone commented ‘bombastic side-eye’ when I shared this senior photo on Instagram. The photographer was aiming for a ‘gentle gaze,’ but my resting b*tch face was not cooperating.” — Leah Wise (remember her week of outfits?), Texas
Thank you for sharing! Does anyone else have iconic school photos? We want to hear about them.
P.S. Readers share their favorite birthday celebrations and 11 reader comments on childhood memories.












