For starters try to make sure you are not trying to stuff too much fabric into the boots. The skinny pants will fit better. You can also get boots with side zippers to help in putting them on without having to keep pushing the fabric down. I also have boot socks that are knee high and I can put them on over the pants bottom to help the boots go on easier. Hope that helps.

Couple of things that helped me:
o Wearing capris tucked into socks as my skinnies. This cut down on the painful ankle bunch I frequently get with full length jeans
o Allowing the jeans to bunch a little bit just above the boot. If I wore them too tightly tucked in, my knees would often get very sore if I had to sit for any length of time. (First time was on a 5 hour flight and it took me awhile to realize what was hurting.)
o Hemming the skinnies for flats also cuts down on the extra denim fabric that needs tucking.
o Zippered boots are a must (for me)

Great I will try these suggestions.