Indiana & Kentucky Parents Share Their Love-Hate Relationship with School Dress Up Days

The Joy and Challenges of School Dress-Up Days

Now that my daughter is out of elementary school, I can finally address the elephant in the room: dress-up days.

I have such fond memories of the smiles, laughter, and fun we had coming up with some of those outfits. But let’s be real—there were also tears, frustration, and the occasional meltdown, especially when I wouldn’t run out to buy something special at the last minute. And then there was Crazy Hair Day. Oh, the horror.

She would spend hours on Pinterest, hunting down the most elaborate hairstyles imaginable—things you know were done by professional stylists. Unicorn horns, rainbows, egg baskets, helicopters, skyscrapers—name something ridiculous, and someone had turned it into hair art…

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