[7] In the strip as written by Segar, Olive is a scrappy, headstrong young woman (her age varying between her late teens and 26) visually characterized by her exaggeratedly slim build (evolving from its previous more realistically proportioned form by the late 1920s) and her long black hair (usually presented as rolled in a neat bun, like her mother's).

Debuting on December 19, 1919, Olive was the childhood sweetheart and more-or-less fiancée of original Thimble Theatre protagonist Harold Hamgravy (Ham Gravy), a "lounge lizard" or slacker type who did as little work as possible and was always borrowing money.

His attraction to other women—particularly if they were rich—naturally incensed Olive, leading her to (in a storyline run in mid-1928) succumb to a fit of "lunaphobia" (a kind of angry madness) over one of his amours; when she recovered, she continued to pretend to have the disorder to win him back.

Olive and Popeye initially greeted each other with animosity (her first words to him being "take your hooks offa me or I'll lay ya in a scupper"), leading them to fight bitterly for weeks before finally realizing that they had feelings for each other.

Unlike most modern damsels in distress, Olive Oyl is tall and skinny, with tightly wound hair and enormous feet (the latter sometimes used to comedic effect).

Despite being officially replaced by Schreffler, Questel later returned to voice Olive Oyl for a 1983 commercial promoting the Popeye video game.

[10] In her Famous Studios appearance, Olive is given more hair, smaller feet, wider eyes, a more feminine face, a tomboyish streak and a slightly less silly personality.

In later animated cartoons from King Features and Hanna-Barbera, while they would occasionally retain aspects of her Famous Studios incarnation, such as her hairstyles, Olive generally reverted to her original enormous feet, pinned-back-with-a-bun hairdo, tall flat brown boots and white socks.