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The key is to find a hat that isn’t dramatically floppy, but a little more stiff; that way it’s just as functional as it is stylish. While cowboy hats are a great option, they don’t exactly achieve that laid-back beach look you might be going for on vacation. So, a neutral straw topper that’s midsize is your best bet. If you’re more sporty, however, any type of baseball cap is fair game. Find one with a slogan or floral print to make a real statement.