Sean Wotherspoon x Nike Air Max 97/1 (2017) for me.
Sean, a long-time vintage Nike collector, was selected along with 11 other Nike-lovers to design their own Air Max sneaker for the 30th anniversary of Air Max Day.
Nike would release their designs to the public and allow them to vote. The winner would go on to see their sneaker be produced and released to the public.
Sean was also the co-founder of the sneaker store Round Two. At the time, his store was the most popular sneaker store in the country. He used that as leverage to market his design. From 2015-2017 Adidas' Yeezy Boost was seen as a big threat to Nike so he made the slogan "More Air, Less Boost" and gave out t-shirts for free at Round Two.
He won the contest the release of his sneaker sold out instantly and resold for over $1,000. The sneaker is still seen as one of the most iconic sneakers of all time and in my opinion, the best Air Max of all time.
I was close with the Round Two team and Sean at the time and was able to see the whole process unravel, spending almost every day with them at the store. That being said, definitely a meaningful sneaker to me.
edit: The shoe is the first and only Air Max 97 (upper) and 1 (midsole/outsole) hybrid ever.