It's not always as difficult as it might seem, depending on the type of hair one has - this troper has hair to the small of her back and can conceal it under a baseball cap if necessary. However, it's very uncomfortable and doesn't look at all natural.

It usually depends on how tight a hat you're wearing: a loose bucket cap is easier, but it still takes a lot of poking at your hair to get it to sit less lumpishly.

This trope actually suffers a bit from RealityIsUnrealistic. It actually ''is'' possible to get really long hair into really tiny spaces, especially if you have straight hair, which can be wadded as tight as a ball of silk.

This (male) troper has very long hair, 3/4s down his back, and it is quite thick... despite that, he has been able to fit it up into a baseball cap for a job (apparently males with long hair in a deli is bad, but females with long hair is okay). However he needs to keep the baseball cap very loose, and its pretty obvious from certain angles that he has a bunch of hair tucked up in his cap.

A good amount of hair can be concealed by braiding it in one or two plaits (depending on the thickness of the hair) and pinning them flat to the head in coils. It is not so easy to do The Reveal that way, through. It takes up a little more cubic space overall than straight wadding, but relatively little away-from-the-head space. (It also works to cushion the back of the head from blows.) Alternately, there's wadding it up in a hairnet under the wig or hat, which keeps it contained a little better and somewhat less tangled. (This troper's hair is to the small of her back and counting.)

This troper and her best friend made a stupid decision in the second grade. We were able to take our long hair and shove it into the hoods of our jackets and pretended to be ''BOYS''. Not a smart idea. Might have worked, except for one thing. And no, it's not that our hoods fell off. This troper had a pink Barbie jacket on.

troper Oh, screw it. ''I'' have hair that is just over three feet long (read: to my thighs), and I'm capable of concealing it under a hat. However, the hat usually has to be more "forgiving" when it comes to being sat on the head; I can easily hide my hair under a cowboy hat or a sun hat, but it's impossible to do with something that is tightly fitted to one's head. A baseball cap is ''definitely'' out of the question, though I'd probably be okay with a helmet.

As a helmet is supposed to be tight fitting (or at least snug), I doubt that you could get your hair into a helmet that you could also wear with it in, say a simple braid down your back. Note that is is not a good idea to put things between your helmet and your skull, including hats and hair, anyway.

This troper can fit all 3+' length hair inside a hat, but it must be a hat with some stretchability (tuque or beret.) For some reason this results in more mixed gender pronouns in conversations.

One of the girls in my college class keeps her hair tied back all the time, she suprised me one day when she took her hair down and it was long enough for her to sit on.

My family has had at least three cats that had fur that seemed to break the laws of physics. HumanTorch2

Stuffing my afro under a do rag and luckily the caps I wear are fitted for when my afro is packed down.

I've got a jewfro and can say for certain that when it's still as ringlets and really not that frizzy it doesn't look that long...but any attempt to brush it or a humid day means that it resembles a giant ball of cotton stuck to my head

This troper has thick, waist length hair that she can twist into a bun smaller than the size of her fist and hold in place with one hairclip. It does have to be a pretty huge hairclip though; those little dinky ones won't work.

this troper before switching to dreads had long hair about half way down his back, which when working would twist it up under his hat, hiding it compleatly.

This Troper's afro kinky hair can very easily go from neck length to as short as two to three inches.

This Troper used to have very long, thick GodivaHair. In order to keep it out of the way and to keep it from freezing, she would wear it in a bun, hiding the volume. Then she would let it out. She also used to have to cram it all up in and equestrian helmet for competitions. She could only to so for about ten minutes without getting a headache. Until she got a bigger helmet that is.