This essay explores Stephen Dedalus’s evolving aesthetics in A Portrait of the Artist as a Young Man and Ulysses, arguing that his early artistic failure stems from his idealization and typification of women. In Portrait, Stephen’s abstract  aesthetic  theory  is  undermined  by  his  inability  to  apprehend  the material reality of women, exemplified most clearly in his treatment of his mother. In Ulysses, his perception begins to shift as he is confronted with the social and embodied dimensions of womanhood. The essay concludes with a reading of Molly Bloom, who symbolizes lived, non-idealized womanhood— complicating Stephen’s earlier scorn for the mother in Portrait—and embodies the mature aesthetic sensibility Stephen must embrace in order to transcend patriarchal abstraction.