Can’t pull of a giant floppy hat? Try a fedora. Like the floppy beach hat, the fedora is another classic, says Roberts. Wolford is also a big fan, “You can wear fedoras with anything casual. The fedora is also season-less, so depending on the fabric/color, you can wear it year round.”

This versatile hat also has plenty of hairstyles that work with it. “Girls can do a low bun or a low side pony,” says Todorov. “But my favorite look is a fishtail braid. It’s hard to learn, but once you know it, you’ll use it all the time.” (To learn how to create a fishtail braid, click here.)