Ankle boots can be worn with skirts, pants, leggings or tights. Long skirts and maxi skirts should cover the top of the ankle boot. Shorter skirts paired with ankle boots should be at least a few inches above the knee. Boots with taller shafts should be worn with shorter skirts.
Any full-length pants can be worn with ankle boots, but only straight-legged pants should be tucked into the boots. Skinny jeans or tight leggings are ideal for fitting into ankle boots, while wide-legged pants create an undesirable bunched effect. Tights and leggings can be worn under a skirt that exposes too much leg between the hemline and top of the boot. Socks can be worn with ankle boots to make them more comfortable, and a visible sock under a pair of causal ankle boots is stylish.
If black ankle boots are worn with lighter colors or short dresses, a dark jacket works well to balance the look. Black ankle boots complement a black dress, and the pairing can be finished off with black leggings for a monochromatic style. For less formal events, ankle boots can be worn with a cocktail dress
Clothing that should not be paired with ankle boots includes shorts, mid-length skirts, pencil skirts, capri pants, cropped pants and cropped tights.