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For most of their history, eyeglasses were seen as unfashionable, and carried several potentially negative connotations: Wearing glasses caused individuals to be stigmatized and stereotyped as pious clergymen (as those in religious vocation were the most likely to be literate and therefore the most likely to need reading glasses), elderly, or physically weak and passive. The stigma began to fall away in the early 1900s when the popular Theodore Roosevelt was regularly photographed wearing eyeglasses, and in the 1910s when popular comedian Harold Lloyd began wearing a pair of horn-rimmed glasses as "The Glass Character" in his films.

Since, eyeglasses have become an acceptable fashion item and often act as a key component in individuals' personal image. Musicians Buddy Holly and John Lennon became synonymous with the styles of eye-glasses they wore to the point that thick, black horn-rimmed glasses are often called "Buddy Holly glasses" and perfectly round metal eyeglass frames called "John Lennon Glasses." British comedic actor Eric Sykes was known in the United Kingdom for wearing thick, square, horn-rimmed glasses, which were in fact a sophisticated hearing aid that alleviated his deafness by allowing him to "hear" vibrations. Some celebrities have become so associated with their eyeglasses that they continued to wear them even after taking alternate measures against vision problems: United States Senator Barry Goldwater and comedian Drew Carey continued to wear non-prescription glasses after being fitted for contacts and getting laser eye surgery, respectively.

Other celebrities have used glasses to differentiate themselves from the characters they play, such as Anne Kirkbride, who wears oversized, 1980s-style round horn-rimmed glasses as Deirdre Barlow on the soap opera Coronation Street, and Masaharu Morimoto, who wears glasses to separate his professional persona as a chef from his stage persona as Iron Chef Japanese.

Many NBA players wear lensless glasses with thick plastic frames like horn-rimmed glasses during post-game interviews, geek chic that draws comparisons to Steve Urkel.

In superhero fiction, eyeglasses have become a standard component of various heroes' disguises, allowing them to adopt a nondescript demeanor when they are not in their superhero persona: Superman is well known for wearing 1950s style horn-rimmed glasses as Clark Kent, while Wonder Woman wears either round, Harold Lloyd style glasses or 1970s style bug-eye glasses as Diana Prince.