I debunked the myths surrounding Cleopatra’s sexuality here and here. Suffice to say that these are not rooted in historic fact or even ancient propaganda. To be fair, Roman propaganda was the first step down this path as it called her a whore for her affair with Caesar, and a sorceress for marrying Antony, just as she became a megalomaniacal tyrant in Roman poetry penned after her death. But the modern idea of an Egyptian queen languidly seeking out sexual adventures does not come from these older traditions which focus on her ambition and amoral pursuit of politically connected suitors. They originate in Renaissance and early modern fiction which dramatized the life of Cleopatra. This is a bit like if 500 years from now, people analyzed works like 300 to understand Xerxes’ fixation on piercings or Gladiator to discover how Commodus was stabbed to death in an arena by Russell Crowe who wanted to bring back the Republic.

Having said that, there is absolutely no good reason to assume that Cleopatra was bisexual because she was promiscuous (or that a person is promiscuous if they are bisexual). Both of these conclusions have more to do with sexual stereotypes than with any kind of objective analysis. It is a pernicious stereotype which equates bisexuality with sexual voraciousness. To circle back to what we know of the historical Cleopatra’s sexuality, there is nothing to suggest that she was bisexual. We only know of two romantic or sexual relationships in her life, with Julius Caesar (intermittently c. Late 48/early 47 BCE – March 44 BCE) and Marc Antony (c. 41 – 30 BCE). Plutarch and Josephus imply that she took an interest in Gnaeus Pompeius Minor and Herod the Great, respectively, but historians tend to discard these claims which are not repeated elsewhere and seem highly improbable.

To be fair, there is a lot we do not know about Cleopatra’s life and it is fair to suggest that her only interest in Caesar and Antony was purely political (although there have been arguments that she loved either or both). Ultimately it does not matter as we can not actually know one way or the other, and her having two love interests of the opposite sex would not preclude her being bisexual for obvious reasons. Her interactions with women at her court are never said to include romantic encounters although she did have women in her close circle of confidants including her handmaidens: the Greek Charmian and Iras (of Nubian, Greek or Jewish origins depending on what theory on the etymology you subscribe to). These two joined her in suicide and upheld their duty to the highest possible level, but these are apparently non-sexual bonds, homosocial if you will.

It is also worth noting that there was no Greek concept of a heterosexual/homosexual spectrum of identity which was determined by sexual attraction. Even if someone was attracted to members of both sexes, they would not identify as being any fundamentally different than someone who was strongly attracted to the opposite sex. There are relatively few references to female/female sexuality in Greek literature as a result of the patriarchial tendency for Greek literature to deliberately overlook women’s private lives and perspectives. The division of the sexes in Greek society contributes to this imbalance as we can mostly only view Greek women from the perspective of Greek men. Having said that, we do have a few scattered allusions to women who were attracted to or were intimate with women to work with. For instance, Lucian’s Dialogues with Courtesans includes a few liaisons between courtesans and women who hire them. Generally Greek authors describe women who desire women as “having the desires and passions of men”.

All of these tend to assume that women’s sexual relationships with women would mirror that of men with women on a social and physical level. This is generally attributed to the confusion which male Greek authors seem to have had with the idea of female/female couplings. What these do not tell us is how women saw these interactions as we have no way of knowing if these simply project how these male authors saw relationships, or if socialization and sexual interactions actually mirrored that between men and women or men and men. We do not even know if Greek men would have acknowledged romantic or sensual interactions between women as legitimately sexual given the phallocentric definition of sex that was emphasized. There have been theories that pederasty, socially sanctioned relationships between Greek men and male youths, had its equivalent among women but this is based off scattered archaeological evidence.

All of this boils down to the issue that we know painfully little about the private lives of Greek women. Greek women interacted in the public sphere considerably more in Hellenistic Egypt but this has not really illuminated our understanding of women’s sexuality that much. So all I can say about Cleopatra is that we have every reason to believe that she was what we would view in modern times as heterosexual and I would be willing to hang my hat on that assessment barring some archaeological revelation, but no one can definitively tell you what was in her head.

Now to address the idea that she cross-dressed. There is no ancient source which implies that she dressed as a man. Technically, she would have worn unisex clothing like himations (Greek robes for men and women) but she never dressed in clothing that was coded as “men’s outfits” in Ptolemaic society. Part of this is because that fashion in the Greek and Roman world was quite a bit different than the modern or even Medieval world. Men, women and children dressed primarily in what was essentially big, single pieces of fabric or cloth. These might cut into different shapes, fastened differently or adorned in myriad ways, but there were no tailored suits and dresses for gentlemen and ladies to get dolled up in. In many ways, Egyptian fashion was more gendered than Greek clothing, although Egypt was more gender-inclusive than Greece. Given that Cleopatra was a Ptolemaic Greek ruler, Alexandrianism with its largely Greek fashion was the biggest influence on her wardrobe. So supposing that Cleopatra had decided to grab Marc Antony’s piece of wool tunic or chiton and wrap it around her body, it would not be obvious that she had done so. Now I do not want to give you the impression that there were no gendered Greek garments as that would be inaccurate. For instance, veils and mantles were essentially for women, and armour was gendered as male. On the whole however, there were no ball gowns for Greek noblemen or waistcoats for Greek men as fashion was considerably simpler.

We do have one account of subversive or socially transgressive fashion from Cleopatra’s life, and that is an anecdote in Plutarch’s Life of Antony recounting how she and Antony would dress up as slaves to go door-to-door pranking people. However, such slave clothing would also presumably be unisex. The transgressive aspect here was two aristocrats dressing below their station in order to engage in childish pursuits, and the anecdote should probably not be trusted outright either since it is first mentioned more than a century after Cleopatra and Antony’s deaths.

The earliest appearance of Cleopatra cross-dressing that I know of in Western literature is from Shakespeare's Antony & Cleopatra. The play includes a scene where Cleopatra refers one occasion where Antony wore her mantle and clothing, and she wore his sword Philippus. This is an example of some of the gender-bending and crossdressing themes which are commonly found in Shakespearean plays. Shakespeare was heavily inspired by Plutarch’s portrayal of Antony and Cleopatra’s relationship as a playful, affectionate, unstable affair. Shakespeare took these facets of Plutarch’s accounts and made them his own by remixing and adapting them into a tragic romance which was politically and socially relevant to Britain at the turn of the 17th Century.

There are other lines throughout the play which might reference the idea that Antony and Cleopatra dressed up in each other’s clothing, and a line at the end of the play speaks directly to the English tradition of having boys act in women's roles during Shakespeare’s day. This line is uttered by a dying Cleopatra who imagines how she and Antony will be parodied and ridiculed posthumously on-stage, including herself portrayed by a “squeaking Cleopatra-boy, in the posture of a whore”.

I think that this line also speaks to us quite a bit. We may have moved past times when women could not act on stage respectably, but modern portrayals of Cleopatra still seek to transform her from a political figure to an amoral and conniving woman whose only successes were a result of manipulating powerful men with sex. She is still cast “in the posture of a whore”, even in media which pays lip service to acknowledging the complications of her political and personal lifelike HBO’s Rome, Assassins Creed: Origins and Liz Taylor’s Cleopatra.

At the end of the day, if Cleopatra had really been promiscuous or openly bisexual or both, it would not detract from her status as a historical figure. It is however relevant that misogynistic literary tropes are the only reason why Western media frequently portrays her as promiscuous in the first place.