I don't think that is a thing I often do.
I do listen to Christmas songs, when it is Christmas, but it would be weird if I listened to that in April.
There is this song from my country called what can be translated to "The Autumn", and I have sometimes randomly sung or listened to that song, when it isn't autumn.
and sometimes I listen to kpop songs about a certain season or weather, even though it's not how the current season or weather is like.