Winogrand was a street photographer known for his portrayal of America in the mid 20th century. He documented the city and the urban landscape, concentrating on its unusual people and capturing odd juxtapositions of animate and inanimate objects. His photographs catch that odd moment where unrelated activities coincided, and it is the nature of these juxtapositions that sets his work apart from other photographers.
Winogrand said that if he saw a familiar picture in his viewfinder he "would do something to change it" - something that would give him an unsolved problem. He would step back or change to a shorter lens, which gave him more facts to organize, and changed the meaning of the facts by changing the character of their setting. He was interested in how small in relation to the total field can the most important part of the subject be and still be clearly described; Or, more precisely, how is the meaning of the most important part of the subject affected by everything else within the frame.
For his book, Women are Beautiful, Winogrand photographed women on the streets of New York. He pictured them going about their business, unaware that they were being photographed. The women pictured are determined and fierce, and not necessarily feminine or beautiful. The pictures seem to be less about a particular subject than where the subject lies in space and how the light falls to illuminate them and their surroundings.
Comparing apparently contradicting statements statements on the nature of photography by Edward Weston and Garry Winogrand, one can see that they express a shared fascination, central to the work of each, in the difference between photographs and the world they describe, and in the possibility that the former may nevertheless, if good enough, tell us something important about the latter.
Fragment from Winogrand: Figments from the Real World by John Szarkowski