The way I see it, you can only rock it if you a) were at Woodstock and practice free love or b) are Mischa Barton.
Which presents a problem: Yes, Mischa Barton is the reason that I feel a need to wear a white men's Hanes tank top underneath everything I wear, including formal and/or cotillion dresses. But at the same time, Mischa Barton tried to convince me to wear Keds. My mom wears Keds. Or at least she did, in the early 1990's. They came from a craft show and had puffy-painted Christmas lights on them.
Usually, the hippie headband is some sort of braided leathery affair. Think Blair Waldorf meets Pocahontas. But if you're Mischa Barton, you whip out your Bedazzler, start a celebrity headband line and sell the version at left for $90.
Or you go to Forever 21, spend less than $6, and Bedazzle it yourself. Preferably with the Marisa-Cooper-makes-her-final-exit-while-"Hallelujah"-plays-YET-AGAIN episode of the OC on in the background.
And in other news, I sort of love Mary-Kate Olsen's headband here. And not just because she's Mary-Kate Olsen. Well, mostly because she's Mary-Kate Olsen. But also because it's made out of peacock feathers, which most people say are unlucky, which is somewhat tragic, because I find them pretty, and I appreciate MK's attempt to prove luck wrong, although I tried to do the same thing, and then the strap of my peacock-y tank top broke at the Funk Groove Lounge. So there's that.