Needs Help!!

This is SOOOO not me, but I need help!  I bought two pieces of clearance items at Old Navy and I have no clue how to "winter-ize" them.  Not that I need to worry about winter temperatures right now, BUT I did purchase them for the Fall and bought a pair of cowboy boots to go with them.  Not sure I can pull off the look, but here it goes........

Look no. 1....

Boots by Alberto Fermani
Scarves & Wraps by Old Navy

OK, so.....what color tights would you wear?  For some reason, I'm not loving the bare legs with this ensemble.  I've seen pictures of people pulling this sort of look off, so I guess I'm trying to re-create it....  poorly, I'm sure, but nevertheless, trying.....  so HELP!

Look no. 2......

Longsleeve Tops by DKNY
Boots by Frye

This skirt is really cute and was super cheap on OldNavy.com, but its a tad bit short.... like when I bend over, just a little too short for my comfort... not that I plan to go bend WAY over in front of someone or get in an compromising position, BUT with 3 little boys, I want to be modest AND be able to move around without constantly making sure I'm not shining my hiney.... but it comes down to top of my knee/mid knee when I'm standing straight up, so no one worry!  Its just short for me!   Anyway, I need to know what color tights you'd put with this.  I am clueless and don't plan on wearing the skirt until I have some tights and I really want to wear the skirt!!