[Answer] What daring 1920s dress was often paired with a bob haircut?

Step 1 : Introduction to the question "What daring 1920s dress was often paired with a bob haircut?"

...Among the most iconic 1920s fashions, flapper dresses had dropped waists and higher hemlines than society was used to. Popularized by Coco Chanel, flapper dresses showed women’s bodies more naturally than corsets and other uncomfortable fashions. Flappers were often criticized for rejecting the Victorian views of their parents in favor of going to jazz clubs and practicing a new standard of personal freedom.

Step 2 : Answer to the question "What daring 1920s dress was often paired with a bob haircut?"

Flapper dress:

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