The “Robin Hood Hat”, aka a “Bycocket” or “Chapeau a Bec”
It evolved from a type of Medieval hat often worn by sporting men, hunters and hawkers included. The first artistic depictions of it appear to have been in the early 1300s. It appears to be most associated with dashing, athletic and adventurous young men, perfectly so for Errol.
Here is a superb site detailing its history in the Middle Ages, with an outstanding visual record.
larsdatter.com…
Mirror Back in Ivory, ca. 1300-1330, Presently at the Louvre

The Smithfield Decretals of Gregory IX, ca. 1300-1340
www.bl.uk/manuscripts/Viewer.aspx?ref=royal_ms_10_e_iv_f078v…
Woman Protecting a Unicorn, ca. 1425-50

The Provost of Aquileia, ca. 14th or 15th Century

The Cardsharps by Caraveggio, 1596

Fairbanks: 1922

The Huntsman, from Snow White, 1937

Flynn: 1938

And here is a previous EFB post and thread discussing the hat’s connection to “Liberty”:
www.theerrolflynnblog.com…
— Tim