If you follow teachers on Instagram at all, you’ve probably seen Outfit of the Day posts. Teachers are sharing what they wear, how they style it, and how they bring personality into their classrooms—and we love seeing all of it.

This is what inspired us to launch the $99 Amazon Challenge. With this new We Are Teachers series, we’re challenging teachers to create something fun, practical, and totally school‑appropriate—all for $99 or less using Amazon finds. Sometimes that means an Outfit of the Day. Other times, it might be a classroom setup, a DIY project, or a creative teacher hack. The category can change, but the budget doesn’t.

When we invited Hilary Statum, a teacher in Tennessee and the creator behind Pencils to Pigtails, to take on the challenge, she came back with a unique DIY to pair with her outfit.

How Hilary Spent Her $99

Here’s everything Hilary used to bring her look together:

Her total purchase actually came in at less than $99!

DIY Pencil Shoes? Yes, Please!

Hilary is known for her colorful, crafty style, and instead of just putting together an outfit, she asked us: “Would you be interested if I made my DIY pencil shoes?”

The answer was an enthusiastic yes.

Hilary created an entire outfit AND custom pencil‑themed shoes, all while staying under the $99 limit. We loved the results. We think this would make a fun teacher bestie party for decorating shoes together, and we especially like that it’s an alternative to painting.

Why We’re Loving the $99 Challenge

What we love most about the $99 Amazon Challenge is seeing how teachers use creativity—not big budgets—to make something their own. We’ll be doing more Outfit of the Day challenges in the future, and we’ll also have some other $99 teacher themes that go beyond clothes.

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