Fall and winter footwear is nothing without boots. Whether you normally gravitate to a flat, Chelsea style or a chunkier platform, one thing is for certain: Kitten-heel boots should not be overlooked.

The shape was popularized in the 1960s—Audrey Hepburn was frequently seen wearing kitten-heel pumps with her ladylike ensembles—and mod-style boots of the era often possessed the short heel as ...