The newer buildings look better. Though, admittedly Tokyo is not known for stunning architecture. However, recently nicer buildings have been built. Nagoya and particularly Osaka are known for having more modern "futuristic" looking buildings. In Tokyo buildings are (necessarily) really fat, and until recently, not too tall. This may change now. They'll be really fat and tall like Yokohama Landmark Tower.
The idea was to get the maximum amount of space, without building too tall due to structural concerns in an earthquake... however, understanding of how to do this better has much advanced over the last 15 - 20 years, as Tokyo Sky Tree can attest. It is also really fat and super tall