My mom gave me an old-time gypsy shag with bangs. (I will show you sometime, but I don't feel like uploading pictures right now :P). That haircut works perfectly with that style.
The trick for perfect messy surfer hair is to do nothing to your hair except brushing and maybe blow drying (upside down drying) and using the right products to keep your hair looking like you just came back from the beach, but controlling the frizz and messiness of it.
What I use to get that look is FX Surf Head Extreme Texturing Paste. It controls frizz and keeps the shape of your style while making a beachy, undone wave. Rub this in your palms and run fingers through your hair. Then flip your hair upside down and shake your head. Then scrunch and place pieces where you want them and ta-da!
That's all you really need to achieve surfer hair, you could also go swimming in the ocean, or a salt water spray would do good. You just need the right products. It's a very simple style and you're sure to love it!