“Ugh. First day of kindergarten. Who picked this out? The bowl cut makes it even worse.”
“This ‘sailor’ dress was the choir dress I had for this Chinese school I was a part of as a child. I LOVED this dress and thought I was so fancy in it. To top that off, underneath that fresh bowl cut were also freshly shaved off eyebrows. Late night infomercials are not good on an 8-year-old’s easily swayed mind, especially the infomercials about shaping your eyebrows.”
“Senior year 2000. Let’s run down the list: overly gelled hair, puka shell necklace, Blink-182 shirt, baggy cargo pants, and chunky skate shoes. Not pictured: wallet chain and blue Quiksilver flexfit hat worn ridiculously askew.
“This was somewhere in the 2007-2008 range. I’m on the right. Chunky earrings!”
“I really thought I could participate, but I just looked and it appears I was never a risk taker, even then.”
“Sketchers? Check. Harry Potter backpack from before the movies came out? Check. Sparkly, randomly bleached jeans? Check. This look was so fire in 1999.”
“First day of fifth grade, September 1988. I thought my outfit looked SO cool. Miniskirt over leggings PLUS scrunched socks. White Keds, of course, and that neon paint splatter shirt. I guess it was colorful, if nothing else. I felt pretty good about it the time, so I guess that’s what matters.”
“Ripped jean skirt and top with matching heels. Fake and bake tan and please return to Tiffany’s dog tag.”
“I can almost certainly guarantee that shirt had No Doubt or Blink 182 on it. Shell necklace, butterfly clips, and a smug closed-lip smile so you couldn’t see my braces. I thought I was cool af. This would have probably been sophomore year, 2002.”
“My senior year I was DEEP into my emo phase. We wore uniforms so technically this wasn’t my first day outfit but it was my ID and yearbook photo. My yearbook quote was ‘It’s called ukulele screamo and it’s art.’ Easily the biggest regret of high school.”
“It was a sad, sad sixth grade year!”
“Ah yes. Kindergarten in my grandmother’s homemade dresses. I think this was ’05.”
“Here’s my eighth grade back to school outfit photo (we had photos the first day). This was 1996 and I was trying to grow out my hair. I’m wearing one of those super cheap and stretchy (poor quality) Delia’s dresses inspired by the ’70s that went to my thighs. I had white knee-high white tights to match the look with Mary Janes. Cheeeeeesy!”
“I think I was going for some sort of Hannah Montana vibe, not completely sure what was going through my head.”
“Tie dye days ????”
“I think i still have that zip-up somewhere, lol.”
“I just want some love for this Garfield lunchbox, y’all.”
“Lookit this spiffy child — it’s my little brother, flexing some Vision Streetwear, I believe. These days, he wears EVEN MORE POCKETS.”
“Acid wash jean dress… white tights… boots… I thought I was the PEAK of fashion and ready to slay first grade!”
“First day of school in 2004: My brother, looking like Guy Fieri with the flame button-up and attempted flipped-up bangs, was starting sixth grade. And I’m wearing a clip-on tie?! I was trying to look ‘punk’ like Avril Lavigne for my first day of eighth grade.”
“I’m the one on the far left. I don’t know what’s cringier: the denim vest or the bangs.”
“First grade. Homemade dress from my grandma and my thick ’80s bangs…I loved it all! Also, take note Miley…I started the tongue out trend.”
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