I was drawn to this photo because of the wonderful button design on the younger woman’s hat. What a creative way to use little pearl buttons! Her older companion’s outfit sports many buttons too, not only running up the shirtwaist dress but also on the pocket.
It would be a lot easier to date this photo if we could see the skirt lengths. Given the boxy structure of the younger woman’s jacket, my best guess is sometime in the mid 1940s. The older woman’s shirtwaist dress style was also quite popular during the war years. Her eyeglass frame come from at least a decade before.
Little hats, tipped at an angle, were all the rage in the mid forties. The older woman above hadn’t quite mastered the rakish tilt.
Try as I might, though, I couldn’t find another example of a hat with buttons.