Okay, so thinking about this, there are a couple of things.
#1. Will you honestly wear skirts/dresses in the winter? I won't. Fall and spring, yes, but not once there is snow regularly on the ground.
#2. Long shorts, culottes, etc. see #1 above. Worn without tights = frostbite.
#3 ankle pants. See #2 above.
That leaves true long pants. Skinnies, straight legs, boot cut and wide legs.
Wide legs are not great with snow, and neither, really are bootcut unless the bootcut is more baby boot in nature and can be stuffed into snow boots.
I have been thinking about this for a while and realized this is why I get bored in the winter. The cold weather can just stay away for a while longer!
I am sticking to my tried and true pant uniform bottoms and investing in more interesting tops and perhaps shoes as I carry my shoes into work.