How and when did fedoras arise as acceptable headwear?

Question

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?

Answer 1

Jewish men have worn a plethora of hat wear, but the popularity of the fedora seems to have stemmed from the last Chabad Lubavitch Rebbe, R. Menachem Schneerson. R. Schneerson's adoption of this hat, which would influence the hat wearing of fellow Chabad members, is historically marked to his ascent in becoming the seventh Lubavitcher Rebbe, after the death of the previous rebbe (R. Yosef Yitzchak) in 1950. As Maya Balakirsky Katz writes, in The Visual Culture of Chabad:

...after the death of his father-in-law, Schneerson actively campaigned for popular favor over his brother-in-law Shmaryahu Gourary. When Yosef Yitzchak's widow demurred from gifting her late husband's signature Hasidic fur hat (shtraymel) to her younger son-in-law, Schneerson adopted the far more American black fedora, which eventually became the standard Chabad choice.

By this time, the fedora had already become a stylish American hat for men, popularized by Hollywood male stars (cf. Humphrey Bogart); as a personal aside, I would guess that the glorification of the gangster in film noirs made the fedora probably the least feminine hat imaginable by this time. Whatever R. Schneerson's intentions for adopting this now American hat, its influence was huge and engendered its own mythology. As a January 13th, 2006 editorial from the Haredi Yated Neeman newspaper once put it:

...there are certain defining articles that link us to our ideology...One of these signature articles of clothing, if not the most distinguishable one, has been the fedora-style hat. The black hat. It is what marks a ben Torah, and distinguishes him from all other segments of Jewish society. From the time President John F. Kennedy shucked his fedora at his 1960 inauguration ceremony and replaced it with the new look of freedom, the black hat assumed a heightened significance in society at large. It is the declaration that we still cling to the old generation; we still embrace the old values that we were taught and are not embarrassed to be called "old-fashioned black hatters.

Ironically, what once displayed a new direction for a religious movement, marking the transplantation of a Chassidic community into a new land, would later become a prime signifier for unassailable tradition.

Answer 2

The law regarding wearing men and women's clothing is dependent on the time and community. What is upheld as His Garment now that hat the fedora was worn by men and women. Just different styles, both called "fedoras" it became part of a dress style looking culture difference sectsin.
different movements continued that tradition. The same is with the long black coat that many Jews wear. Because it is held that we must look respectable before God at all times so they will this Garb which includes the dress fedora hat and either a jacket or coat.