This trophy can be difficult to keep track of, as you will sometimes have drinks that you didn't buy from a machine, and they do not count towards the trophy. There are numerous vending machines throughout Tokyo that carry different drinks. Fortunately, you do not have to buy each drink from every vending machine; you only need to buy one of each unique kind. The list of vending machine drinks are:
Some machines are hidden in the subway, but none of the drinks should be exclusive to those.
Not all drinks will be available to purchase from the get-go, so you will have to check back towards the end of the game. Since these drinks don't contribute much gameplay wise, I advise not purchasing any drinks during your playthrough, and instead grab all of these in one go.
All credit to xNinjaOfChaosx