12 Outfits from School Picture Day You Probably Regret
These fashion choices seemed fine at the time, but now they live on forever in your most awkward photo memories.
- Chris Graciano
- 3 min read
Everyone has that one school photo that makes them cringe—and chances are, the outfit is a big part of it. From wild patterns to questionable accessories, school picture day brought out some seriously regrettable looks. These once-trendy ensembles are now a hilarious time capsule of what not to wear.
1. Neon Windbreakers
keen on Pexels
In the ’90s, the louder your jacket, the cooler you thought you were. However, those hot pink and electric green windbreakers now scream “fashion emergency.”
2. Turtlenecks Under Graphic Tees
Satumbo 9 on Pexels
This odd layering choice was somehow all the rage. A cartoon shirt over a too-tight turtleneck was peak elementary school drip.
3. Denim Overalls with One Strap Down
Anastasia Shuraeva on Pexels
Overalls were in, and wearing one strap undone meant you were edgy. However, in photos, it just looked like your outfit was falling apart.
4. Bowl Cuts and Matching Vests
TONI&GUY PONDICHERRY on Pexels
Pairing a crisp vest with a geometric pattern and a bowl cut was a recipe for retro regret. You looked like you were auditioning for a kid version of The Matrix.
5. Loud Hawaiian Shirts
Мария Кашина on Pexels
For some reason, dressing like a tiny tourist was a school picture trend. You wore bright florals, an oversized fit, and absolutely no context.
6. Sweater Vests Over Dress Shirts
Polina Tankilevitch on Pexels
An attempt at being “dressed up” often meant stiff collars and itchy fabrics. The result? A forced smile and a squint from all the discomfort.
7. T-Shirts with Cheesy Slogans
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Nothing says regret like a shirt that reads “I’m Not Listening” or “Future Rock Star.” What felt like an attitude back then now reads like a cry for help.
8. Over-Gelled Spiked Hair
Mike Jones on Pexels
Hair that could double as a weapon was totally in. However, those sharp, crunchy spikes now look cartoonish, and they didn’t move. Ever.
9. Puffy Sleeved Dresses with Lace Trim
Fatjon Shullazi on Pexels
Girls in the ’80s and ’90s often rocked these pastel nightmares. It was all puff, no chill. They were part princess, part doily.
10. Matching Tracksuits
Capualondon on Wikimedia Commons
Whether velvet or shiny polyester, matching top-and-bottom sets were oddly common. They were coordinated, but not classy.
11. Plaid-on-Plaid Combos
Muloki Peter on Pexels
Mixing multiple plaid patterns wasn’t just allowed—it was encouraged. Clashing flannels and pants gave you the lumberjack look without the beard.
12. Oversized Jerseys (Even If You Didn’t Play)
Kaone Makoko on Pexels
Wearing a football or basketball jersey for picture day made you feel sporty, even if you never touched a ball. They usually hung down past your knees.