Hatless Jack

Neil Steinberg's Hatless Jack is a quick read full of interesting anecdotes that exhaustively covers the rise and fall of hat fashion in America. What's really useful is its excellent bibliography.

Google Hats

There are a remarkable number of works on hats available through Google Books, some with just the bibliographic information but many full text, out of print works too.

Books About Hats

The Village Hat Shop has a good list of book resources. They might be available through a library near you.

The Bowler

The bowler resonates with such historical and social significance that it's impossible to capture its importance in a short post. Indeed, F.M. Robinson has written an entire book on the subject:
The Man in the Bowler Hat: His History and Iconography, cataloguing its adoption by: "Gamekeepers, squires, street vendors, omnibus drivers, counterjumpers, bankers, union men, women on horseback and in cabaret acts, detectives and hanging judges, dictators and bums." Charlie Chaplin, Laurel & Hardey, Rene Magritte, Samuel Beckett, Herge, Anthony Burgess, and Milan Kundera used the bowler as a symbol both instantly recognizable and endlessly mutable.
The Bowler (or Coke or Derby) was created in 1850 by Mr. Lock of St. James Street. The "iron hat" was coated with shellac and was, I imagine, more social signifier than comfortable headdress. Remarkably, it came to be associated with both everyman and the ruling classes, with both men and women, and hence its long lasting appeal. (see magritte, smith)