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The different types of ankle boots Dressier Ankle Boots: Usually have a pointy toe and a stiletto or a skinnier heel Must be neutral color in suede, leather, or patent leather Wears well with suits, jumpsuits and skinny or wide leg trousers, or pencil skirts Try these: Sock, Pointy-Toe, Kitten Heel, Block, and Stiletto Tip: You can also wear a flat, pointy-toe bootie as a more stylish alternative to a ballet flat, the pointy toe makes the low heel much more formal than just a basic flat boot, which is more casual