The gold is 1950s, I call those "Shar-Pei" or "wrinkle dog" hats! That was a briefly popular style in the mid to late 1950s. The navy straw is really wonderful, as it resembles an antique lady's riding hat. Hard to be exact as it is a classic style, but it looks late 1950s to early 1960s to me. That Woodmere label was in use in the 1960s, but hats with a Woodmere label were also around in the mid 1950s.