I can't narrow it down to just one shoe.
TMac 2's. Those shoes are just straight-up sick (although I also really liked all of TMac's shoes except for the 5's).
The original D-Wades from Converse (the white/black/red version). Never owned these ones, but always wanted a pair.
Also, since I was always a baseball player above all else in high school:
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Nike Air Huarache 2k5 cleats. Easily the most comfortable spikes I ever wore, and they were also flashy and VERY durable. I had the black/silver and the grey/black versions my last couple years of high school. Gave the black ones to a kid on a team I was helping my dad coach because he couldn't afford new ones. But I'm never giving away the grey ones.