'eS Penny 2 reissues showed up today. I missed out on this shoe because I had stepped away from skateboarding in the early 2000s when it was originally released. I had several pairs of 'eS shoes during the 90s though and generally liked them.
The materials and construction of the upper appear better than average quality compared to what you get these days. The upper is suede and there is decent thickness in the toe and ollie area. The suede is quite flexible which surprised me. The upper is not stiff in the toe like some shoes made of nubuck or synthetic materials. The parts that matter are triple and double stitched, though there are a lot more seams in the toe area compared to newer skate shoes. This does not bother me because I was never the type of person to completely shred my uppers. With most decently made shoes, I would wear out the sole first and the upper would only have some ripped stitches and a small hole.
In terms of fit I would call these wider than most skate shoes today. There is plenty of width and volume throughout the whole shoe IMHO. Even with the very thick, puffy tongue, there is enough room across the forefoot and toe area. Length seems TTS. Heel lock is good when the shoes are laced to the top and the laces are tightened properly. There is some decent padding around the ankle.
The shoes feel generally okay with the thin stock insoles but they don't provide enough arch support for me. I tried some 3.5mm FP orthotics and they fit in the shoe fine without cramming my feet. I'm not sure if I could get a 5mm FP in there or not. The 3.5mm should be sufficient for these shoes because there is some decent midsole cushioning. If you have a narrow foot, these shoes are probably not for you.
Overall, I would say the shoes are nice. One thing I didn't like were the extra long laces. They are too long for me and wouldn't work for skating. I can easily replace those but I'm mildly disappointed that a $110 pair of shoes in a fancy box did not come with an extra set of laces. There were also some loose threads under the insoles that didn't look great. Again, for the price I would expect this stuff to be cleaned up before the shoes get boxed up and shipped out for retail.