The question is," said June critically, looking out of the window to the street where a fine drizzle of rain was falling, "does one, or does one not, wear one's best hat to go out and meet the one and only man one has ever loved?" She turned round and looked at Esther with a little nod. "That's grammar, though you may not think it, my dear," she said. Esther laughed. "I should say one does wear one's best hat," she said decidedly. "Especially seeing what a very charming hat.
Hats, especially blocked hats, can be fragile, so the question of whether to wear one in the rain for an important date was a complex one. And until the 1960s, the question wasn’t whether to wear a hat, but which one to wear. Going out in public without one was going out not fully dressed.
This is from a truly silly novel by Ruby M. Ayres called Phantom Lover from 1921. If you read P.G. Wodehouse, this is the real-life counterpart of his fictional Rosie M. Banks whose books do not tear at the heart-strings, but yank them into a knot. I could barely finish it as the coincidences piled up to such a degree that I was laughing too hard whereas the book takes its love plot very seriously. June, unfortunately, is not the heroine of the book or it would have been a better and much less silly book. Instead, we get the sappy Esther who is poor but proud, and a chump when it comes to men.