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Most Frequent Wear: Nike Air Penny 2 (2008)
“Growing up, my good childhood friend’s parents bought him all the latest sneakers he wanted. He was the first to get the original Question in middle school, and he was also the first to get the original Nike Air Penny 2 as well. My family was never about spending over $30 for shoes as a kid, so I had to live vicariously through him as a teen. When these re-released over a decade later, it was a no-brainer. One of the original pair I first bought when I started buying sneakers, so they have gotten the most mileage.”
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