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Accessorize with style by adding a cute hat to your outfit. You can pull off a hat, even if you have short hair, as long as it's the right hat. A head that completely covers your head and hair won't be as flattering on you as a hat that allows a bit of hair to peek out. You should also keep your face shape in mind when choosing a hat to wear. Your hat doesn't have to match your outfit perfectly, but should coordinate with it well.