Fashions during the 20s and 30s were very different than today. Women always wore dresses, flapper style with dropped waistlines ending in knee length skirts, or shirt dress style which had natural waistlines but longer in the length. Before the day of nylons, silk stockings were worn under their skirts even though the knees might be baggie before the end of the evening. Not a pretty sight.
Hats and gloves were worn at all times for social occasions. They wouldn't be caught outside their homes without a hat. Might not be such a bad idea to cover up a bad hair day...
The most popular hat style of the day was the cloche hat, from the French word for "bell". The cloche, then, was bell-shaped, hugging a woman's head ending just above her eyes. It was often made of felt and would fit snugly on her head to keep her hair in place while traveling by car, an often windy prospect. In summer the cloche was frequently made of straw for the warmer weather.
A cloche hat worn during evening social events could be decorated with bead appliques to match evening attire. This type of head dress is often equated with the flapper fashion. Who wouldn't want to look like this to paint the town?
How would they travel with all these different hats in their wardrobe? Wherever women traveled they would be accompanied by their trusty hat boxes. Hat boxes were often built to closely resemble the shape of the hat - often round shaped. The hats would carefully be positioned to cushion any sudden movements of the box, inverted in a hole suspended off the bottom of the container. Maybe that's why people didn't travel all that much back then. Can you imagine lugging all that added luggage through airport security today? The lines would be even longer than they are now.