Ok, maybe I didn't read the thread carefully enough and this has already been said, but here's what I would do. (I lived in Ohio and Seattle before AZ, so I'm familiar with walking around in lots of cold and wet).
- wear snow boots for outdoors
- bring (or keep at destination) nice shoes for indoors
- before leaving home, grab bottom of pants so that excess fabric is in one place
- wrap that excess fabric around leg, so that the silhouette of the pants looks like skinny jeans at the bottom (no "crushing" involved)
- carefully slide foot into boots
- change into dress shoes when arrive at destination
By folding the excess fabric on the pants (rather than cramming it into the boots), things shouldn't get wrinkled. If they do, try tucking the bottoms of the pants into thick socks before putting on the boots, that way the pants won't be able to move.