The problem of how to define beauty is central to Troilus and Cressida. Shakespeare depicts Helen as incapable of acquiring symbolic stature and this creates in the play questions about the nature of beauty.

In the world of Troilus and Cressida beauty is defined by the beautiful woman, whether it be Helen or Cressida. But the idea of Helen as the archetype of beauty seems to have been challenged very early by shifts in perspective. The poet Stesichorus was legendary for a poem defaming Helen, for which the gods blinded him. He recanted and recovered, as Plato records in both The Republic and Phaedrus. Stesichorus' palinode asserted that the Helen story was a fabrication:

Dio Chrysostom, a first-century critic of Homer, declared that Homer was a beggar who told lies for a living and that the Judgement of Paris was an unlikely tale, in the first place because the 'consort of Zeus' would not have required Paris, a mere shepherd, to testify to her beauty, and secondly, because Helen was Aphrodite's sister, and the goddess would not have wished to disgrace her. Dio claims that Helen was lawfully married to Paris: 'If anyone does not accept this account under the influence of the old view, let him know that he is unable to get free of error and distinguish truth from falsehood.'