I noticed this too, a lot of Japanese society feels like it's stuck in the 90's. Even the little things like the graphics made for ads. Probably has something to do with having a conservative culture and the demographics/economic issues that began becoming a problem around then
After living more than 7 years in Japan, I think it's that a lot of Tokyo's tech infrastructure is build around the persona of a 45 year old male office worker and his specific needs. For example, Pasmo cards can be used to buy drinks (and other things) at the train station in addition to paying for the tickets.
