a clean solution that I found, where I'm working with some constant file extensions.
from pathlib import Pathclass CaseInsitiveString(str): def __eq__(self, __o: str) -> bool: return self.casefold() == __o.casefold()GZ = CaseInsitiveString(".gz")ZIP = CaseInsitiveString(".zip")TAR = CaseInsitiveString(".tar")path = Path("/tmp/ALL_CAPS.TAR.GZ")GZ in path.suffixes, ZIP in path.suffixes, TAR in path.suffixes, TAR == ".tAr"# (True, False, True, True)