Q. While I know every trend I like is not for me, I am enamored with ankle boots paired with skirts (particularly pencil skirts) for work. I am 5 feet 3 inches tall and curvy, and my legs are of course short. Can I pull off this look? Also, should I look at boots that hit right at the ankle or those that come a bit higher?
A. The most flattering way for a petite curvy woman to wear ankle boots with a pencil skirt is to look for ankle boots (or booties) that dip down in the front, showing off more of your leg. Avoid any booties that come above the ankle bone. Look for slim heels, rather than chunky heels, to offer a more flattering look for your legs. Also, it’s best to pair them with skirts that hit above your knees, or right at the top of your knees, to help elongate (and visually slim) your legs. Here are some booties worth trying: