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

Sammy Keach

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.

Once—just once—I attempted a unicorn horn. It was passable at best and a disaster by the end of the day. I fought back tears the entire time. After that, she begged me repeatedly to recreate that horn, but no way. She can save that trauma for her therapist one day. We switched to "rainbow hair" using pipe cleaners. It's fine. Everyone's fine. We're all fine.

Now she’s older, and her school dress-up days are a bit more manageable - PJ day and favorite Christmas character day. As much as I miss those moments of childhood, I’m at peace with this chapter being over—it wasn’t always the easiest.

A Month of Dress-Up Days: Fun or Frustration?

Just the other day, I saw a Facebook post that summed up so many parents' feelings about dress-up days perfectly. At my daughter’s old school, they’re apparently celebrating the countdown to Christmas with a month of dress-up themes. Good golly, Miss Molly. And my friend Vanessa didn't hold back on how she feels about the daily struggle.

She nailed it when she wrote:

“Nowhere in Dante’s Inferno did they talk about the ring that is school dress-up days.”

The comments were a goldmine of solidarity: Nicole asked why schools torture parents with a month of dress-up days during the busiest time of the year. Michele admitted to deleting the email after getting completely overwhelmed by the schedule. Emily joked that whoever made the schedule clearly doesn’t have children. And Denee shared a lifesaving tip: gather all the outfits in one spot in the closet for easy access.

But Nikki summed it up best for all of us: “Is it too early for a margarita?”

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Love or Hate? The Dress-Up Day Debate - Indiana and Kentucky Parents Weigh In on How They Feel About School Dress-Up Days

Now, I didn’t want to assume that all parents feel overwhelmed by dress-up days, even during the season's chaos. After all, this is the time when we’re juggling recitals, buying gifts, cleaning the house, hosting parties, and cooking up a storm. Some parents might really be into fashioning a snowman complete with arms, a top hat, two button eyes, and a carrot nose out of hair at 6 o'clock in the morning...

So, I decided to ask the question on our station page: How do parents really feel about dress-up days? Do they love them or loathe them? The responses didn’t disappoint!

Ashley McReynolds channeled her inner Grinch: "Hate! One week is fine but two weeks or more is crazy!"

MaJesta Knox lets her daughter decide: "This was 50s day for the 50th day of school. I think they have gotten a little excessive but it's all in fun. My little lady doesn't always wanna participate so I let her decide."

Emily Gray got really honest: "I was a horrible mom and forgot half of them."

Mary Nell feels like dress-up days are a gateway to Walmart pajama shopping: "Most of them I loathe!! Why must they have pajama day?? I believe that this makes people believe they can go shopping in just their pajamas."

Jessica Scherer Skyles isn't doing a Target pickup at 10 pm either: "I have a love-hate relationship with these days because my daughter wants me to go buy her stuff to wear every day, and I can't afford it. We do our best to make sure she gets to participate in some of the days, but two weeks is a lot."

Sami Jones said it's even worse down south: "My kids love it! I do too! McCutchanville picked days like “red and Green Day” so it makes it easier for families that can’t go out and buy new for one day. We just moved here from Nashville and the dress up days there were insane and always had to buy something new."

Shelbi Elizabeth November is sorry, not sorry: "It’s way too much. I’m thankful my kids are older and no longer participate lol."

Ashley Morgan Holley gets creative with items from around the house: "Anyone that hates it is taking it too seriously. I don’t go out and buy stuff just for dress-up days. If we have it, they wear it, and it’s fun!  Pajama day is the best one! Fun, comfy, and simple!"

Sammy Keach wants them to break free: "Love them! Especially because we wear uniforms, plus my kids have fun being festive!"

Tara Groth doesn't care for the abstract: "If they’re easy, sure. Favorite team shirt Dress up like a snowball fight."

Crystal Flahardy is over here thinking about how good the rest of us have it: "Mine never really do it but when they do, I love it."

Samantha Rae likes this or that days: I love dress up days when they are things most every child has… our school is doing this or that so it gives more options for the kids!

Amy Yeager West wishes she could do dress up days too: We loveeee dress up days, it’s less stressful when I let me daughter be creative and come up with her own outfits. It’s also very entertaining. Tomorrow is tree topper day so she’s wearing a fun headband… pajama day may be my favorite, makes life easy that morning mismatch day is another easy one… put on whatever you want I don’t care the photo was western day, and we were able to recycle an old outfit her grandma wore when she was young, so that was fun!

Stephanie Williams gave us a teacher's perspective: As a teacher, I despise dress up days. It makes the kids crazy. They enjoy it though. But I’m a fun sponge. As a parent, I hate it! It causes too much anxiety trying to search and search for the right thing. I’m not buying a whole new outfit every dress up day.

How Schools and Workplaces Use Dress-Up Days to Spark Joy

On the flip side, I’m genuinely grateful that our school system tries to sprinkle a little fun into the school day. Kids need that—especially during this time of year. They need something to look forward to, a reason to get up and make the trek into that building.

When my daughter was in elementary school, I volunteered the week before winter break every year. It was such a joy to see the kids looking adorable in their outfits, bubbling with excitement as they chatted about their costumes.

And it’s not just for the kids! One year, my workplace joined in the fun with a week’s worth of dress-up days. Let me tell you, nothing beats the hilarity of stepping onto the elevator in a reindeer onesie alongside corporate types in suits and pumps. It was pure magic.

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