Last fall and winter I had not a single pair of skinny jeans to my name. But I had a beautiful pair of boots. I stuffed my jeans into my boots every way imaginable with some success and a lot of failure.
This winter I have a few pairs of skinny jeans, (thank goodness!) but still a ton of regular boot cut or flare jeans that I would also like to wear. Here's my tips on what worked and didn't work for me.
First, you want to choose jeans that have a moderate to minimal flare. I have one pair that flares out quite a bit and I don't even care to try to make that not look like a bunchy mess under my boots.
Second, choose your method. You can fold and cuff your jeans like the picture below (I, for the life of me cannot get this one figured out.) or you can take a big loose rubber band or an elastic headband wrapped twice (this is what I do) and cuff your jeans and then fold all of the excess over and rubber band it. See photos below. Either way, it is best to secure your jeans with a nice, long sock.
I love these boot socks with the lace or knit that pops out the top. Good luck! If you can plan your outfits to wear your boots with your skinnies, that is so much easier and faster. :)