Yes I know it's a bit early. But I'm currently looking for Christmas programming. Music or otherwise. Asking now gives sometime to plan things.
Here're some things I play around Christmas.
I have a folder that contains non-traditional and novelty Christmas songs, mostly from the 1950s & 1960s - I call the resulting programming a Slightly Bent Christmas, and play it in place of Billboard Hits and Misses, Lost Jukebox and Jazz.
I also try to play Christmas-oriented Old Time Radio, taken from the OTRR (Old Time Radio Researchers) Archive. There are lots of applicable shows, and most are in the public domain.
The site librivox.org has lots of Christmas audiobook short stories - even some longer ones - which are in the public domain. Everything from Charles Dickens to Arthur Conan Doyle to authors you've probably never heard of.
May not be what you're looking for, but hopefully gives you some ideas.
Last year I made a folder of Christmas songs like songs the Carpenters did, Beach Boys did a Christmas Album, Darlene love's well known album of Christmas songs, Elvis, Brenda Lee, Stevie Wonder and others. I had about 100 songs in my genera and they played several times an hour for about 3 weeks in December but I deleted the folder after Christmas last year and may not be in the mood to compile a new playlist and schedule it for a few weeks. We'll see. Not even November yet.
One of the problems with an oldies station in general is playing songs that are now 'out of favour' so to speak with the current culture.
Baby It's Cold Outside is one. I personally don't see the harm, particularly as an attempt to recreate the past, but some do take it seriously.
In my regular song rotation, I'm sure there are lots of other currently politically incorrect songs. Again, I generally ignore the issue (and sometimes even revel in it), except for the truly outrageous imo (such as Indian Giver by Bobby Curtola - great music, but unfortunate lyrics).
Then again, I'm an ancient Western culture male so what do I know?