If you’re an avid follower of educators on Instagram, you’ve likely come across the popular Outfit of the Day (OOTD) posts. Teachers are showcasing their attire, sharing styling tips, and infusing their classrooms with personal flair—and we can’t get enough of it.
This vibrant community inspired us to introduce the $99 Amazon Challenge. In this exciting series by We Are Teachers, we encourage educators to create something engaging, practical, and completely school-appropriate—all for $99 or less using finds from Amazon. While one challenge might focus on a stylish OOTD, another could center around classroom decor, DIY projects, or innovative teacher hacks. The theme may vary, but the budget remains consistent.
We had the pleasure of inviting Hilary Statum, an enthusiastic teacher from Tennessee and the creative mind behind Pencils to Pigtails, to take on our challenge. She responded with a fantastic DIY project that beautifully complemented her outfit.
How Hilary Spent Her $99
Here’s a breakdown of everything Hilary used to complete her look:
Surprisingly, her total expenditure came in under $99!

DIY Pencil Shoes? Yes, Please!
Hilary is celebrated for her vibrant, crafty style. Instead of simply assembling an outfit, she proposed, “Would you be interested if I made my DIY pencil shoes?”
The response was an enthusiastic yes.
Hilary crafted an entire outfit AND custom pencil-themed shoes, all while adhering to the $99 budget. The outcome was nothing short of delightful. We think this concept would make a fantastic gathering for teacher friends to decorate shoes together, and we especially appreciate that it offers an alternative to traditional painting.

Why We’re Loving the $99 Challenge
What excites us most about the $99 Amazon Challenge is witnessing how teachers leverage creativity—not hefty budgets—to craft something unique. We plan to host more Outfit of the Day challenges in the future, along with additional $99 themes that extend beyond clothing.
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