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Attempting a messy ponytail always goes one of two ways—it can look awfully atrocious or all kinds of awesome (like the adorable one Rebecca Breeds is sporting). If your goal is the latter, make sure you keep these three tips in mind:
1) ALWAYS ADD TEXTURE. Steer clear of stick straight strands; the messy look works best with loose curls and soft waves. Get the look by manipulating your hair's natural texture with a styling product, like a salt spray, curl cream, or wave pomade. Then twist your hair into three or four tight top knots to help enhance the s-pattern.
2) USE YOUR FINGERS. Combs and brushes are of no use here. Bend over and hang your head before raking your hair up into the desired ponytail position with your fingers. Loosely secure the base with an snag-free hair elastic. (The end result won't be as nice 'n neat as it would have if you'd used a traditional styling tool, but of course that's the point.)
3) ADD A FEW LOOSE TENDRILS. A few well-placed face-framing pieces lend extra credibility to a purposefully messy mane. Windblown, wispy strands help tie the whole look together.