The 50 Greatest Tennis Sneakers of All Time

1. Nike Air Trainer Hi

Year Released: 1987

The first time I saw the Air Trainer Hi, I think I think I might have had a small stroke. I distinctly remember having some sort of sensory crossover and wanting to taste the shoe or something. I thought it would taste like marshmallows and mint leaves. Right. Enough about that. These shoes did have a very strong smell though, that has always defined fresh out the box for me. The 2002 re-issues had the same smell. I almost passed out. When reissues popped, I was fiending so badly, that despite having knocked my back out of wack a couple of days before, I loaded up on painkillers and took a car service to Fulton Mall and back. I went home with four pairs, because I wanted to be able to wear this shoe for the rest of my life.

The Air Trainer Hi is so plush, so soft, so comfortable that it's almost like wearing bedroom slippers that perform. The price you paid for this privilege is that you could melt through the outsole in under a week. I wasn't caring though. When this shoe launched, it was confusing to me. I didn't know what it was. I think that was the genius and the risk of launching a "cross-training" category/product. Was it a tennis shoe? McEnroe wore it. I always called them McEnroes. Andre Agassi wore them and so did Vitas Gerulaitis and Mats Wilander. Maybe it was a basketball shoe. It was a mid, and it appeared to have a lot of cushioning. I've seen a number of shots of Jordan wearing it chilling after practice. Maybe he wore it to practice too. It was also deceptively light. You could definitely run in these. Maybe they were just street shoes. Cash Money wore them on his album cover. A lot of people still think of it as the Bo Jackson, and Bo knew a lot of things. Maybe it really did cross into everything.

Point is, the shoe and the entire initiative was going to do one of two things: either (a) be Lou Roe— a tweener—great little shoe, but not clearly “this” and not clearly “that” and ultimately very confusing to the consumer; or (b) convince the consumer that whatever you wanted to do, the Air Trainer Hi was just right for that. From my perspective, what kicked it over into option (b) (aside from the stellar marketing) was flawless design by Tinker Hatfield. There are a lot of articles on the design inspiration and process for this shoe. I think the biggest change was the move to the more prominent and traditional toe overlay. The original design for this shoe, and some of the player samples, had a plain toe that reflected the prevailing training/workout look of the era. It looked a little bit, um, aerobicized. At some point between sample and production, the toe changed to a more traditional overlay construction. To me, this made the shoe speak not only training and exercise, but also basketball, running, tennis, etc. Perhaps more importantly, it made what was a very aggressive, new and innovative looking shoe slightly less risky for the kid to wear on the block. That's big, because all of a sudden the shoe moves from performance to lifestyle. Purchasing decisions move from need-based to want based. And I wanted every fucking color. The Air Trainer Hi came in more colorways than you think too, including two different all-over black elephant print versions. Ultimately, the Air Trainer design language set the stage for most of what Nike did from 1988-1994, crossing over into basketball and inspiring things like the Jordan III. If I had to wear one shoe for the rest of my life I would wear the Air Trainer Hi.

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