Winningham has contributed to various photographic projects over the years, most notably the project funded by Seagrams and Company to photograph the county courthouses of the United States. The project, which culminated in the highly-praised book, Courthouse, brought recognition to Winningham for his architectural photography.

Beginning in 1980, however, Winningham began to develop a serious interest in the culture of Mexico and began traveling there extensively. By 1982 he had virtually given up black and white photography, his preferred medium of the 1970's, and turned instead to color, both in his still photography and films. In 1986 he published a book of color photographs of Houston, A Place of Dreams, on the occasion of the city's 150th anniversary. In 1987 he produced a book for Rice University, for the seventy-fifth anniversary of the university. After those publications, he began to focus his efforts in still photography almost entirely on the subject of Mexican fiestas.

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