A. True, ankle boots, or booties, are everywhere this fall, worn with everything from skinny jeans to dresses and skirts. This doesn't mean it's a trend for everyone, however. Those with shapely calves may have a hard time wearing ankle boots with a skirt or dress since the boots tend to make even thin calves look a little thicker. If you're petite or have short legs, be aware that booties will chop inches off the length of your leg, though this can be compensated for with a high heel.
If you think you're ready to give ankle boots a try, here are some chic options:
1. Wear your ankle boots with skinny jeans
2. Wear them with dresses or skirts that hit just above the knee or higher, below the knee is harder to pull off. You can wear this look bare-legged or with opaque tights.
Here are a few visuals, on the left is from shopbop.com and the rest are from bananarepublic.com: