Whether you are wearing a dress, skirt, or a pair of pants, we can all agree on one thing: Ankle boots are made to be shown. Don't hide them under your maxi dress, long skirt, or your wide leg jeans. I love boots in general, but I find ankle boots more appropriate for my height, because I am only 5'5". I look like I have longer legs when I wear them, especially when I wear them with a fitted sweater dress. Having your long skirt flapping on your ankle boots could be a nightmare.
Consider your colors when buying your ankle boots. I tend to stay away from brown because it is too close to my complexion. Make sure you pair your boots with the right colors when pairing them with skinny jeans or leggings, because you have to tuck them inside the boots so all the details on the boots can show.
Ankle boots are always in, so invest in a pair of boots that will last you a long time. I love ankle boots with a side zipper for easy access. A little embellishments also work for me.