This thesis uses the photographic portrait as an example of contemporary art practice to examine developments in aesthetic sensibility and constructions of meaning with particular address to ineffable qualities in both the subject and in the photograph. It examines the contribution of practice to a wider cultural debate, predominantly described as poststructural. Thomas Ruff's contention that it is impossible to photographically depict an individual, establishes a methodology that interrogates assumptions and directs examination toward reconfiguring issues of theory and practice. In the photographic portrait, what is `essential' equates with the expectation of visual statements that are definitive and what is 'ineffable' is that which transcends words. The persistent premise of capturing the 'essence' is dependant on the notion of 'presence', the certainty of pure perception or essential meaning, now undermined by poststructuralism in terms of conceptions of meaning and authorship. If essential depiction is problematic, how might a correlative adjustment to conceiving and validating photographic meaning be framed? How are essential or ineffable qualities displaced, formed and manifested? What constitutes the contemporary 'meaningful' portrait? Realigned as 'depictions of people', the 'portrait' serves a complex function, adjusted in the light of psychoanalysis and poststructuralism and visibly manifested as metaphor for contemporary consciousness. With particular reference to texts by Julia Kristeva, Emmanuel Levinas, Jacques Derrida and Jean Baudrillard, this thesis demonstrates photographic practice as a form of discourse that visualises implicit truth-values, and participates in debate. It asserts figural interpretations to photographs over literary systems like narrative, and immanent property over aspirations to 'transcendence' or 'essence' and proposes reconfigurations of psychological, critical or poetic 'fiction' as alternatives. It repositions the ineffable as a conceptual domain of possibility that assimilates the dynamic of differance as its poststructural equivalent and proposes a conceptual aesthetic that celebrates aspects of poststructuralism and is rooted in what the photograph provokes rather than what it depicts.