Some artists are more careful in how they paint the great man and will tome down the feminine features and only leave hints and references to other paintings. You have to wonder what is going on here. Is this deliberate, is there some knowledge these artists are tapping into that has been lost through the ages? Perhaps there is some clever and subtle pun at work of which we no longer remember the symbolism but which we've inherited without knowing the source. There are not many references available that allow us to reconstruct what the man looked like and there are various contradicting descriptions regarding his physique. At Wikipedia we find the most tantalizing version by Greek biographer Plutarch (ca. 45–120 AD, which reads as follows:
Historical accuracy gets a bit more complicated with other descriptions being offered. Greek historian Arrian (Lucius Flavius Arrianus 'Xenophon' ca. 86 – 160) described Alexander as:The outward appearance of Alexander is best represented by the statues of him which Lysippus made, and it was by this artist alone that Alexander himself thought it fit that he should be modeled. For those peculiarities which many of his successors and friends afterwards tried to imitate, namely, the poise of the neck, which was bent slightly to the left, and the melting glance of his eyes, this artist has accurately observed. Apelles, however, in painting him as wielder of the thunder-bolt, did not reproduce his complexion, but made it too dark and swarthy. Whereas he was of a fair colour, as they say, and his fairness passed into ruddiness on his breast particularly, and in his face. Moreover, that a very pleasant odour exhaled from his skin and that there was a fragrance about his mouth and all his flesh, so that his garments were filled with it, this we have read in the Memoirs of Aristoxenus
The strong, handsome commander with one eye dark as the night and one blue as the sky.
The semi-legendary Alexander Romance suggests that Alexander suffered from heterochromia iridum: that one was dark and the other light. British historian Peter Green provided a description of Alexander's appearance, based on his review of statues and some ancient documents:
Physically, Alexander was not prepossessing. Even by Macedonian standards he was very short, though stocky and tough. His beard was scanty, and he stood out against his hirsute Macedonian barons by going clean-shaven. His neck was in some way twisted, so that he appeared to be gazing upward at an angle. His eyes (one blue, one brown) revealed a dewy, feminine quality. He had a high complexion and a harsh voice.
Ancient authors recorded that Alexander was so pleased with portraits of himself created by Lysippos that he forbade other sculptors from crafting his image. Lysippos had often used the Contrapposto sculptural scheme to portray Alexander and other characters such as Apoxyomenos, Hermes and Eros. Lysippos' sculpture, famous for its naturalism, as opposed to a stiffer, more static pose, is thought to be the most faithful depiction.Here is another portrait of Alexander on the right, this time a bit more traditional and dressed as the artists of the day assumed he strolled around in his domain (Painting by Pietro Antonio Rotari (1707-1762), Alexander the Great and Roxanne. 1756, Oil on canvas, 243 x 202 cm, State Hermitage Museum, St Petersburg). What we see is a more traditional rendition based on classic sculptural depictions, as if all ancient Romans and Greeks wore togas all the time. More surprisingly is the assumption that legendary heroes went to battle in this manner. Note however the reversal of blue and red/pink between the female figure and the sitting Alexander.
Portraits such as these are re-interpreted versions of older editions and ironically those newer versions are made more manly then their inspirations. The further back you go the more ambiguous the depiction becomes, which brings us back to the original tapestry that started my wonderings about the legendary figure. Here for example is a modernized version of the same medieval tapestry I saw at the Carnegie Museum of Art. The pose, placement, angles and headress are all exactly the same (although horizontally reversed), but the facial features have been altered and modernized. Unfortunately I do not have a high-res photograph of the original tapestry, but I found a decent version in which you would unmistakenly identify the main character as a woman. I leave it up to you to judge what happened in this historical mystery.