Think of compression stockings like a bunch of rubber bands. When you roll or bunch the stocking, all of the material gets condensed into one spot. Then it’s like trying to put a big roll of rubber bands over foot all at once.
The best way to put on compression stockings is to open the top band and step into them like pants. Stop pulling when your foot feels a bit of resistance from the stocking. You’re not going to get your compression stocking on your legs in one pull, so don’t pull really hard from the top. I recommend the use of donning gloves when putting on compression stockings. Donning gloves help your hands grip the material so that you can pull it up your legs little by little.