Spent 10 days in between Osaka and Tokyo. Like some others have said, Tokyo is amazing just to walk around. Several neighbourhoods have restaurant/bar districts organized into city blocks. These blocks are buildings, which take up the entire block, and will have 3+ floors, with nothing but restaurants and bars in them, many will be open at all hours. The majority of the owners will put a great deal of pride into their establishment, so you could spend a lifetime exploring these places and be constantly finding new ones.
The Japanese get swept up in fads, so the themes of many bars and fashion will change. When I was there about 5 years ago, "Americana" seemed to be the fad of the day. A lot of clothes retailers and establishments were orientated towards this theme.
I'd recommend checking out the giant fish market. Even if you can't get in to see the market, which has very limited capacity, the surrounding sushi restaurants will put anything else you've ever eaten to shame.
I'd also recommend grabbing a drink from one of the fancy hotel bars located at the top of their tours. This the one from Lost in Translation:
https://tokyo.park.hyatt.com/en/hote...ewYorkBar.html
The drink will set you back $20-50 for a simple mixed drink or beer. However, the experience is pretty great. Staff will come and pull your chair out when you want to stand up. It's a nice break from the constant go go go of the city below too.