In The Prince, we could argue that Niccolò Machiavelli compares fortune to women for sexist reasons. In his comparison, Machiavelli brings in many toxic tropes about women, including the belief that they are unsteady or "changeful."

The purported unreliability of women is seen throughout history. We see the "changeful" notion in the 1690’s Salem witchcraft trials when women and young girls were accused of changing into witches. We also see this "changeful" notion in the tendency to not heed rape reports from women.

The purported inconstancy of fortune/woman contrasts with the purported reliability of mankind/man. Machiavelli calls mankind "steadfast in their ways." That idea plays into notions that men are somehow invariably reliable, firm, and dependable. Yet look at some of the most visible men in politics and culture -- do they seem steady to you? Would you characterize Donald Trump, Joseph Biden, Kanye West, or Tucker Carlson as stable and balanced?

The sexist parallel continues when Machiavelli declares,

if you wish to keep her [Fortune] under, it is necessary to beat and ill-use her....She allows herself to be mastered by the adventurous.

Here is another injurious stereotype about women: they like to be subjugated, dominated, and treated poorly. Women themselves have been accused of perpetuating this violent generalization. You might want to look into recent criticism concerning how Lana Del Rey's music might glamorize abuse.

However, by the end of Machiavelli's paragraph, we notice that fortune and man might not be so opposite. As it turns out, it's not the "steadfast" man that Machiavelli champions. Rather, it's the "less cautious" and "more violent" young man that Machiavelli supports. That's the kind of man that snares fortune.

If you are "less cautious" and "more violent," aren't you also "changeful"? It's interesting to think about how, in the end, Machiavelli's description of the ideal man who commands fortune is not so different from fortune itself.

Perhaps this is beyond the scope of your question, but you may want to consider employing queer theory. Maybe think through how Machiavelli’s young men could have more in common with fortune than his sexist binary acknowledges.

In chapter 25 of The Prince Machiavelli infamously describes fortune as being like a woman. Fortune is a very important concept for Machiavelli; it's crucial for a successful ruler to learn how to master it. That's not to say that fortune can ever be controlled any more than you can control a river. But just as you can divert the course of a river or build a dam to prevent it from causing flooding, so too can the potentially damaging consequences of fortune be mitigated by taking wise precautions.

In doing so, it's always better to be bold rather than timid. After all, fortune favors the brave, as they say. Adopting such an approach does not guarantee success, of course, but it does increase one's chances. Fortune was often portrayed in Renaissance art as a female figure, forever spinning her wheel (the wheel of fortune, no less). At that time, the prevailing attitude towards women was completely at odds with what's considered acceptable today. Then, it was widely believed that women were physically and intellectually weaker than men and therefore needed to be kept firmly under the control of their husbands, brothers, and fathers. Fortune, according to Machiavelli, must be treated the exact same way.