The stiletto is one of the most culturally complex items in a woman’s wardrobe.
The history of the high heel in Western dress reaches back to the late 16th century when European men first embraced the Near Eastern heel and incorporated it into masculine attire. By the early 18th century, men had abandoned the high heel, and it became an expressly female form of footwear, signifying an enduring range of meanings, from demure femininity to predatory sexuality.
The stiletto appeared only after World War II when fashion sought to bring women into greater alignment with the wartime pinup ideals. By the early 1950s, stilettos had become appropriate — even required — in a wide range of scenarios. Stiletto-wearing women were represented doing things as mundane as household chores or as erotic as posing for pornographic pictures. But they were also expressly not represented as holding positions of power.
The cultural shifts of the 60s caused fashion to banish the stiletto but it retained its erotic currency. When it returned to fashion in the late 70s it was infused with even greater pornographic associations that only increased as the century progressed. Many 80s professional women sought to distance themselves from the stiletto by opting for low heels but they were often ridiculed for this “desexing” choice.
High fashion reacted with a more sexualized form of “power dressing,” complete with toweringly high “killer heels” that insinuated business acumen was not enough to be successful. By the 1990s, many argued that the trappings of stereotyped femininity should be transformed into signifiers of success, including high heels.
The regrettable tweet by Jorge Cortell reflects this long history and suggests that women still haven't achieved equal footing with men. Currently women — and only women — are expected to negotiate the complex meanings that high heels convey. But times do change. Perhaps one day men like Mr. Cortell will feel compelled to embrace their success by donning a pair of killer heels.