These both look fantastic on you. I like the top, too. I think I slightly prefer the blush version but it is difficult to say for sure due to lighting. They both look great.
I hear you on cropped pants in the colder months. Angie's clever styling suggestions are iffy for me, too, for similar reasons. I have found that it comes down to a few options.
1). With slimmer crops...a bootie that had exactly the right shaft height and is slim fitting enough at the ankle so that the shaft simply doesn't "catch" on the pant. This can be hard to find, I admit, and works better when the pant is a bit wider in the calf area, so that there are fewer opportunities for catching itself up on the bootie and getting stuck.
2.) A tall boot, as Joy suggests. Again, this works better with wider crops because slim crops can have trouble fitting over the boot. I did find that knee high fitted boots worked amazingly well with wool culottes in winter...I did wear tights or thermals under those but because the pants were wider, I didn't have the same feeling of "bunchiness" that is the usual reason I don't care for tights under trousers.
I have to admit it is imperfect and I'm not thrilled with the whole business, despite loving crops in theory (and in practice during the warmer weather).