I think you can make a serious argument that Penny Hardaway's signature shoes were on par with Jordan's from the late 90s. That's when Nike really started experimenting with new materials, and the results are stunning.
Everyone already knows all about the Jordans, but I'd like to have a look at Penny's kicks.
Nike Air Up High
These weren't technically Penny's shoes, but he wore them for a while. I don't love them, but they were definitely part of Nike's "squiggly" stage (see the first Pippen's). They look very 90s, and they're alright I suppose.
Nike Air Penny
The first Hardaway signature shoe is gorgeous. I'm a sucker for dark shoes with a white midsole. Plus these were the first shoes to have the 1 Cent logo, which was pretty brilliant.
Nike Air Penny II
I love this shoe. These are easily in my top 10 basketball shoes of all time. I won an 8th grade fre-throw contest in these, and these might be the most comfortable shoe I ever played in. Thankfully, these are being re-released this year.
Nike Air Flight 96
Another of the squiggly Nikes. This was a pretty good-looking shoe, but I remember it being stiff to wear. Love the ice bottom though.
This was a revolutionary shoe made from the sharkskin. The sharkskin part probably isn't true, but this shoe was out of this world. There was a kid named Roy Alexander III (and, yes, he used "the third") who was on my freshman football team that used to wear these to practice. These retailed for $199.99; he wasn't the wisest kid.
Nike Air Penny III
I don't like these, but I suppose they play off the Foamposite + squiggly theme. A little too garish for my tastes. Which are impeccable.
Nike Air Penny IV
That's better. Back to simplicity. As far as I can tell, these are Penny's last signature shoes. Maybe it's because he left the Magic after this season, or maybe it's because his legs started exploding, but I can't find any other Pennys. This is a really good way to go out though. Not too squiggly, not too over-designed. Just a nice looking shoe.
Timeline via The Shoe Game
Pictures via Pick Your Shoes