I recently cut my hair short (chin length with layers) and have found it so liberating to wear my hair loose underneath my headscarves and braid hats. It is long enough to fit into a low ponytail, but now that the weather is getting warmer, I'm enjoying the relaxation afforded by wearing my hair down...
The best wrapping technique for this is the Dutch Crown (see 60-second demo below or watch here). It completely hides short hair at the nape of the neck, since you are crossing the tails instead of tying them. This makes the scarf overlap and 'trap' all of your hair. However, if it's a really breezy day and you want to be extra careful, just tuck the back tail underneath your scarf a bit at the nape of your neck. This trick also helps cover longer hair that would otherwise peek out.
Ashley wearing the Dutch Crown technique with the back tail tucked underneath.
If you are feeling super lazy on a hot summer day, skip the twisting and looping of the tails, and simply cross them at the top of your head. Secure at the nape of your neck with a bow or double knot. Try positioning the untwisted, unlooped crown over the very front edge of the scarf or an inch or so behind it. Avoid crossing the tails at the top back of your head, as they might slip backwards and result in a total, um, headscarf malfunction.
Top view of the untwisted, unlooped crown tied with an XL Island Getaway Scarf
Another super easy technique for letting your hair down: the first few steps of the Twist Bun technique, minus the bun.
Alyssa R. rocking a messy Double Wrap. You could leave your hair loose and reign it all in while crossing the scarf tails.
And of course, a cozy braid hat is the easiest solution of them all...