The new Easyboot Transitions are really fantastic. They are like sneakers for your horse, padded and full of cushion. However all the padding and large gaiter is a bit stiff at first and doesn't want to stay out of the way. I'd try to put them on and it would gather and bunch up. So I "trained" the gaiter which helps to break it in. Several of us on Team Easyboot trained our gaiters, but seems like we all had a different method. I wet the gaiters and rolled them down as far as possible. Then I clipped them into place with clothes pins and let them dry that way.
By having the gaiter flaps out of the way the boots went on much easier, just work them back and forth a bit and they slide on. And after they get used a couple times and broken in, they become quite easy to put on and use.