Go naked under it :-)
wear a warm parka, pants, and heavy boots.
Over the knee boots.
I am partial to pink so I will have to say the pink top that matches the pink in the skirt with the denim jacket...since you are wearing boots with this ensemble (would say the brown ones=earth tone that would go with the floral theme) I think the denim jacket would compliment a casual/cool/feminine style. I am not a fan of leggings with a skirt and cannot help but feel that you should show off your legs otherwise why not just wear pants? Okay, that is just me and I know that it may be very cold wherever you are...best of luck to you!
I suppose then that suffering in the name of fashion is out of the question? LOL...just kidding! It sounds as though the leggings are a necessity then:(
I'd have to see photos of the items you are talking about to see the colors because I would say: wear the pink tank, jean jacket, grey leggings, and black boots - but the colors could be way off and not mesh well (the leggings and skirt.)
I like my original thought, only try to find some cream colored leggings instead of grey and wear the long sleeved cream/white shirt over the pink tank. the pink will still show through a little bit and you will be warmer