20. Nike Air Zoom Generation

When: 2004

Who: Rashad Anderson 

The shoes that started it all — maybe not for Anderson, although he did his thing but we mean The Chosen One. Fresh off his $90 million contract with Nike just months after graduation, LeBron James got laced with the Zoom Generations. At $110 these were on-point performance wise — durable and lightweight thanks to the Zoom Air cushioning.