Stiletto heels, the very thin high heel, were certainly around in the late 1800s as numerous fetish drawings attest. Firm photographic evidence exists in the form of photographs of Parisian singer Mistinguett from the 1940s.
The stiletto heel came into vogue in women's fashion in the 1950s with the advent of technology using a supporting metal shaft within the heel, instead of wood or other, weaker materials that required a wide heel. This revival of the opulent heel style can be attributed to the designer Roger Vivier and such designs became very popular in the 1950s.
The word stiletto is derived from stylus, meaning a pin or stalk. Its usage in footwear first appeared in print in the New Statesman magazine in 1959: "She came ...forward, her walk made lopsided by the absence of one heel of the stilettos".

As time went on, stiletto heels became known more for their erotic nature than for their ability to make height. Stiletto heels are a common fetish item. As a fashion item, their popularity changed over time. After an initial wave of popularity in the 1950s, they reached their most refined shape in the early 1960s, when the toes of the shoes which bore them became as slender and elongated as the stiletto heels themselves. As a result of the overall sharpness of outline, it was customary for women to refer to the whole shoe as a "stiletto", not just the heel. Although they officially faded from the scene after the Beatle era began, their popularity continued at street level, and women stubbornly refused to give them up even after they could no longer readily find them in the mainstream shops.

A version of the stiletto heel was reintroduced as soon as 1974 by Manolo Blahnik, who dubbed his "new" heel the Needle. Old stocks of unworn pointed-toe stilettos, and contemporary efforts to replicate them (ironically, lacking anything like the true stiletto heel because of changes in the way heels were by then being mass-produced) were sold in street fashion markets and became popular with punks, and with other fashion tribes of the late 1970s until supplies dwindled in the early 1980s. Subsequently, round-toe shoes with slightly thicker (sometimes cone-shaped) semi-stiletto heels, often very high in an attempt to appear more slender, were frequently worn at the office with wide-shouldered power suits. The style survived through much of the 1980s but almost completely disappeared during the 1990s, when professional and college-age women took to wearing shoes with thick, block heels. However, the slender stiletto heel staged a major comeback after 2000, when young women adopted the style for dressing up office wear or adding a feminine touch to casual wear, like jeans.

Stiletto heels are particularly associated with the image of the femme fatale. They are often considered to be a seductive item of clothing, and often feature in popular culture.