Some time ago, I settled on an answer: the best way to appreciate Tokyo is to see how it's transformed over time. There is only one way to do that, and that is through a walking tour that begins at Meiji Shrine and ends at Omote Sando. There are 5 main stops (and a million more along the way, depending on how much time you have):
2) Olympic Stadiums: From Meiji Shrine, leave pre-World War II Japan and cross the street to go visit the first symbols of achievement in postwar Japan. The old Olympic Stadiums were home to the 1964 Olympics, and there, you can catch a glimpse of the sense of hope that would have captured a Japan that was rebuilding after the devastation of World War II. Now, they are used for myriad events including concerts, and if you visit on the weekend, you will often find street vendors abuzz selling treats like takoyaki (octopus balls), yakisoba (pan-fried noodles), and dango (mochi balls on a stick).
4) Takeshita Dori: Walk down past Harajuku station and cross the street to Takeshita Dori--the heart of Harajuku fashion and counter-culture. Japan, which is often known for its conservative order, abandons this in the disarray and individuality that Takeshita Dori offers. The street is home to countless boutique shops with fashion ranging from the silly to the outrageous. If you visit on the weekend, be ready for wall-to-wall crowds, but in some ways, the bustle really captures the essence of Takeshita Dori.
5) Omote Sando: When you get through to the other end of Takeshita Dori, hang a right and head back to the major Omote Sando intersection. There, turn left and walk up the hill. Flanking you will be the pinnacle of haute fashion, including Armani, Louis Vitton, Dolce and Gabbana, among others. If it happens to be a hot day, you can escape into the Omote Sando Hills mall for additional high-end shopping opportunities. Of course, Omote Sando still has elements of its traditional character, including Kiddy Land--Tokyo's version of the FAO Schwartz toy store--and myriad small stores that reside just one side street back from the main promenade. There is no shortage of shopping or eateries on the main road and its adjoining back streets.
And there you have it: a trip from prewar Japan, to the Postwar Olympics, to the economic miracle and the counter-culture that emerged from it. You can accomplish this walking tour in as few as a couple of hours, though it is definitely possible to take the entire day to enjoy this unique and important section of Tokyo.