I've collected a few pictures displaying some fine historical Jewish hats:
Jewish students with their teacher in Samarkand, ca. 1910. (Bukharan Jews)
Painting of a Mountain Jewish woman from the Caucuses, (by Max Tilke, early 20th century.)
Detail of a painting by Carl Gustaf Hellqvist, 1882, Valdemar Atterdag holding Visby to Ransom. This man (who is not Valdemar) is wearing a traditional Jewish hat.
Russian Jews in NYC, 1876
A Mountain Jewish man wearing a traditional hat, 1898.
Crimean Karaite men, 1837. Karaite Judaism is distinct enough from the other branches of Judaism that the Karaites managed to avoid some of the legal persecutions against Jews in 19th century Russia, and later used this as legal precedent to avoid the Holocaust (though many still died.) Many Karaites sheltered other Jews during WWII.
Stained glass window of Daniel, Germany, 12th century.
Jewish poet Susskind of Trimberg (on the right).
This picture and the next: Mountain Jews from the Caucuses, 1901 and 1898, respectively.
Unfortunately, not all aspects of history, not even all aspects of hat history, are cheerful. Some hats were voluntarily worn. Others were not. Today, though, many traditional hats are worn with pride. (Even if the winters in Israel aren't quite what they were up in Russia.)