How To Wear Ankle Boots
With skinny jeans or leggings
DO look for flat and heeled ankle boots that dip in the front (like a cowboy boot) or have an asymmetric shaft, so they don’t cut straight across your ankle.
DO slip booties on over skinny jeans and leggings—there isn’t any excess fabric to bunch, so you’ll get a nice clean line.
DON’T cuff skinny jeans or leggings above ankle boots. It looks unnecessary and visually cuts legs at the ankle, making them look shorter.
With loose pants
DO wear pointy-toed, heeled ankle boots under wide-leg and boot-cut trousers. For the most leg-lengthening look, pant hems should hit no more than a half inch from the floor (at the heel) and the point of the toe should peek out in front.
DO wear heeled ankle boots with boyfriend jeans. To retain a little femininity, peg the hems so they hit above your ankle and expose just a bit of skin.
DON’T try to tuck loose pants or jeans in—it creates a frumpy look.
With a skirt
DO wear ankle boots with longer skirts. They look best with of-the-moment hemlines—midi skirts and pencil skirts that fall at (or below) the knee are great options.
DO opt for basic black booties that hit at the slimmest part of your ankle, especially if you’re self-conscious about your legs. The same way nude pumps make calves look long and lean, black ankle boots worn with opaque black tights have an elongating effect (not to mention it’s a classic and office-appropriate combination).
DON’T pair a skirt or dress with flat booties. It will make your legs look shorter than they are.
Courtesy of: http://www.realsimple.com/