I love a giant, wide-brimmed, straw hat for the beach and I can usually find them on sale for a decent price in August. They're kind of classy-looking, they transition from the pool to a restaurant, and they're excellent at hiding stringy beach hair. Plus, they keep the sun off my face which is kind of the entire point of a giant hat.
This year I'm thinking I'll spring $20 and pick up this black and white version from J Crew.
I usually end up with plain black straw (practical!) but I'm kind of bored of that one (and I have two crumpled black straw hats in my closet already). This one looks so much more elegant to me! It's priced half of what it was earlier this summer, and $20 is about my sweet spot for this kind of item.
I've bought several J Crew hats in the past and they've all lasted me several seasons before losing their shape or getting too torn up. Sold!