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One thing that illustrated and photographic archives have taught us is that people have always known how to rock a stylish piece of headwear. From squat caps to towering toppers, history has produced a hat for every occasion. Here are some stylish hats, with a healthy dose of fashion and confidence, could still look just as fabulous today. The sleek, head-hugging cloche is the perfect companion to the bobbed hairstyle worn by flappers.