"squared away" is an idiom which means that something is properly organized/arranged: I need to get all my documents squared away. For instance, if someone has just changed their living arrangements, "squared away" means that they are settling down and getting their place organized and comfortable: The room is squared away already. "squared away" can also mean to fix something: We need to get everything squared away. It can refer to the organization of a group : The military community is perfectly squared away. When you are talking about people "squared away" means ready to tackle the task at hand, having the ability and skills to cope with something: He will make a great ball player when he gets squared away. From my experience, the idiom is not obsolete at all and it often heard in speach and used in literature.

"Getting squared away" is a very common American idiom. It means to "put everything in order / get everything under control." For example: "We're getting everything squared away in preparation for our vacation." (I believe this has its origins in shipping and the navy: to "square away" a ship meant to fill it with supplies and put everything in storage in a secure way. The best way to do this was to put boxes side-by-side, thus "squaring" them)

This is not a standard phrase, so I can only guess what it means. square = old-fashioned Some people were very popular, but now they are turning "square" because a new group or fashion is taking over. The old people are getting squared away. Like I said, it is not a standard phrase, and I think it was made up by the people who said it. Oh well, guess I was totally wrong here. Never heard it in England.