Everytime I do dd1's hair in a ponytail I always get the bumps from the brush on her head, and then the bloody thing falls out in about an hour. She's starting reception on thursday and I would love to know how to do it so I can at least send her to school looking tidy!
I am fairly hopeless at this too - I find it is best if I first of all take the hair from the front and make that into one small pony tail at the top of her head, and then gather that pony tail with the rest of the hair to make a normal sized pony tail at the back. This does not tend to come out! I occasionally try to be adventurous and do a French plait - or even 2 - at it always looks great in the morning but is a mess by 3 p.m. Don't bother with clasps as they'll be lost in the first half hour.
There are two things that really make a difference. The first is that you use a bristle brush as this smooths out the bumps. Secondly use one hair elastic (not the soft ones the proper covered elastic bands) then once that is in put another one over the top of the last making it tighter. (I am now a Ballet teacher so spend my life doing hair!!!)