Pair short ankle boots with a pair of skinny jeans in the same color. Short boots also pair well with short dresses and skirts. Avoid looking frumpy by wearing a dress or skirt above the knee with a flat boot.
Wearing short boots with skinny jeans or pants of the same color helps elongate the leg. If contrasting looks are paired together, like a white pant and black boot, the visual effect cuts the leg in half, shortening the body.
With an ankle boot, heel height should directly contrast dress or skirt length. A higher-heeled ankle boot pairs well with a skirt or dress that hits mid calf, adding height and lines to an outfit. A shorter hem line pairs well with a flat boot for an edgier look.
When wearing skinny jeans with short boots, have the brim of the boot wider than the pant cuff, so the pant can sit comfortable inside the shoe. For boots that have a narrow brim, wear ankle pants, or pants slightly higher than the brim, exposing a hint of skin at the ankle.
A short combat-style boot pairs well with a short feminine dress. To add a touch of grunge to the look, wear a pair of scrunched up wool socks to give the outfit an early 90's feel.