First things first, you need to hunt down a pair of tall boots that will fit your calves. Because if your calves are 13 inches or less, it's not that easy these days. For example I need 13 inch circumference/13 inch shaft - this is how limited my choices are and why I haven't bought new tall boots in years and years: http://www.zappos.com/womens-b.....arity/asc/) .... It will be easier if your legs are long, but not much more.
My suggestion is to find the boots first. Tucking skinnies into tall boots will add some weight to your legs and go a long way towards helping your eye get accustomed to seeing your legs in skinny jeans. Tall boots will do the same for skirts and dresses.
Booties, of course, are an option too. But I've found that adding a chunky bootie that is loose around the ankles has the effect of making my skinny legs and ankles look overwhelmed, and like a kid playing dress up in mom's or dad's shoes. We can wear boot styles that are looser but you really have to watch the proportions to get it just so -- just-right loose, not drowning loose.
Another great option for you, in bootwear, is a boot with tons of scrunch. This will add weight to your legs, like legwarmers added weight to dancer's legs in the 80s! Would you consider cowboy boots? That's another option. (I'm personally debating it myself... )
Get the boots first. Because it may be a long hunt. But once you find the right pair, then finding skirts, dresses, skinnies will be much easier.
