Everyone always says that hats are over rated or cliche and they can be, if they are styled wrong. There are many ways that you can style them. Ashley Tisdale is one of the many celebs that you see walking around Hollywood sporting a fedora. You can dress them up or down.
Dress Up:
You can wear a fedora with a cute solid dress from somewhere like Abercrombie or Hollister, possibly Forever21. You're going to need to have a dress that it tight fitting around the bodice so that it looks more put together. Style it with a solid colored dress, some strappy sandals and your bold fedora.
Dress Down:
You can easily throw on a fedora on with a T-Shirt, a simple pair of flip flops, shorts and then your fedora.
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