Today I learned that the fedora was originally a woman's hat, invented/popularized for women in the late 19th century and only migrating into menswear after 1924 when Prince Edward of England started wearing them.
Per the torah men are forbidden to wear women's clothing (Devarim 22:5), but the fedora is ubiquitous in parts of the Orthodox community so this is clearly not understood as a violation of that commandment. So how did its use come about in the Jewish community, and when? (I doubt we were much concerned with the fashion trends of English nobility.)
Perhaps Jewish use of the fedora is fairly recent and by then it was well-established as a man's hat so its origins don't matter? Is our adoption of it enough later than 1924 for this to be plausible?
Perhaps we say that the fedora, being only about 125 years old to begin with, didn't have a long-standing association with women (just a few decades) so we can disregard that no matter when we adopted it?
Or perhaps the fedoras worn today harken back to something much older, that was always a man's hat, and a late-19th-century fashion fad isn't relevant?
What is the history of Jewish men wearing fedoras?