Tokyo is probably the most English friendly city I have visited. signage and audio announcements are at worst equal occasionally seemed skewed more toward English. Beyond walking a few extra blocks as a consequence of choosing the wrong station exit, I got lost exactly once in my week there. It was a very enjoyable afternoon as I was willing to toss the planned schedule and let Tokyo happen. I highly encourge it.
I return this month, I still know very little Japanese, and fully plan on going out and about with just a map and guidebook.