This article accompanies the fable
Machiavelli would have had none of that. In The Prince (1513) he writes ironically: "it is better to be rash than timid, for Fortune is a woman, and the man who wants to hold her down must beat and bully her. We see that she yields more often to men of this stripe than to those who come coldly toward her."
But what did she look like?
Leonardo has a drawing of her from around 1483 but some would say his Vitruvian Man was where he went next with the concept. Albrecht Dürer also gave it a try around 1502 but he added angel wings and no Wheel of Fortune (below). Compare this with the Virgin Mary on Rubens' moon here.
Originally a minor Greek and Roman fertility goddess, Dame Fortune pops up in Dante's Commedia (Inferno canto VII) where she seems to be a mercantile deity. Virgil explains that she spins her Wheel of Fortune in the affairs of men, and wealth and prosperity come and go but, as he points out in the fourth circle of Hell, there are those among us who have been destroyed by their greed and avarice, Popes and Cardinals among them.
Below is an earlier illustration of Dame Fortune for Boccaccio's influential De Casibus Virorum Illustrium (transl. as "On the Fates of Famous Men" or informally as "The Fall of Princes"). This work was written in the late 1350's and it influenced Chaucer (The Monk's Tale) and anticipates Machiavelli's The Prince, except it is medieval and gruesome, where The Prince is neither.
The illustration below, from a 1467 French version of De Casibus Virorum Illustrium, is by the Coëtivy Master - see the Getty Museum for more of his illustrations.