A photo of a transgender Air Force pilot preparing for Anzac Day has won the 2015 Head On Portrait Prize.

Molly Harris took out the prize with her emotive image of pilot Sandra, born as John, shaving as she gets ready for the Anzac Day parade.

Now a festival including more than 100 photographic exhibitions across Sydney, the Head On Photo Festival began life as the Head On Portrait Prize.

The expansion from the Portrait Prize into a festival has seen the introduction over the years of four new prize categories: Mobile, Landscape, Student, and Moving Image.

First prize in the Mobile category has been won by Laki Sideris, for a sedate, high-contrast black-and-white image from his mother's funeral: an image he cannot remember taking.

Alfonso Perez has won the Landscape division, with his depiction of Indonesian disparity.

Jakarta's largest cemetery, lush with grass, provides a banquet for a shepherd's flock of sheep, whilst the city's tallest ultra-modern building stands monolithic in the background.

Head On is Australia's largest photo festival with a satellite program of talks, workshops and exhibitions.

More than 4,000 photographers entered the five categories offering more than $50,000 in prizes, with some of Australia's leading photographers represented in the list of winners.

Portrait Prize

First place: Being Sandra by Molly Harris

Second place: JOHN by Glyn Patrick

Third place: Sawat by Samantha Everton

Landscape Prize

First place: Urban landscape, Central Jakarta, Indonesia by Alfonso Perez

Second place: Salt 400 by Murray Fredericks

Third place: Bruce Ridge by Andrew Lance

Mobile Prize

First place: Life by Laki Sideris

Second place: Kobani by Andrew Quilty

Third place: Dive Dayclub, Southern California by Justin Vague

Student Prize

First place: Shattered Euphoria by Paul Phillpott

Second place: Suffocating thoughts by Ella Rynehart

Third place: Alex by Hannah Kelly

Moving Image Prize

First place: Stereotypes - What are you listening to? by Dan Gray