Pineappling hair is pretty much what it sounds like: It's putting the hair up on top of the hair so that it looks just like a pineapple. We do this for sleeping (naps and bedtime) in order to keep the bulk of the hair off the side of Boo's head. The hair that gets rubbed against while sleeping, the less likely breakage will occur.
Not all hairstyles can be pineappled. But those that can, we do. These include anything dangling, yarn extensions, twists, box braids, and even free hair (afros).
We start by having Boo bend over so that we can make sure we get the back and sides up and away. The front of her hair is not nearly as important to work toward the top because, well, she doesn't sleep laying on her face.
The hair is gathered loosely into a ponytail holder. (We usually use a scrunchy for yarn extensions, or terry cloth pony O's, but I happen to have one of Daddy's ponytail holders laying around so I grabbed it for the purposes of these photos.)
It should be pretty clear by these photos why it's called "pineappling." Boo knows the term and what it means and will often come get me as she's getting ready for bed, mostly because "Daddy doesn't know how to pineapple very well."
Lastly, you want to make sure that you have a sleep cap that will cover the mound on top of the head created by pineappling. The snugger-fitting caps are great for cornrows and flat twists, but for the purposes of pineappling, we've found that larger satin caps give us the necessary room to hold the hair on top while still protecting her hairline.
Below you can see her hair pineappled from a previous post:
This photo was from when we pineappled her hair while wearing her loose hair. When wearing her afro, we've found that loosely braiding the hair and pineappling it helps keep it's fullness day after day. If we left it down, sleeping on it would cause it to flatten and lose it's volume.
Although I don't sleep with a sleep cap, I do pineapple my long hair at night. It's usually in a messy bun with a scrunchy atop my head. Or I will do a very loose braid, while bending over, so that the braid comes from the top of my head (instead of the back) and then I will lay it toward the top of my pillow so that I'm not sleeping on it. This technique is great for all hair types, as the more friction you place on the hair between your head and the pillow, the more likely it is to break. And if you're a really restless sleeper (as I am) you can multiply that by 1000!