Osman Asaf enrolled in the Sanayi-i Nefise Mektebi in his early twenties. He was among the school’s first students and graduated successfully. He is one of the founders of the Ottoman Society of Painters, the first artist collective in our country. He also assumed responsibility as the managing editor of the society’s publication, the Ottoman Society of Painters Journal. During the War period, he served as mayor of the Bandırma district in Balıkesir. During the Republic period, he taught drawing at numerous secondary and high schools, beginning with the Numune-i Terakki Mektebi. He retired from Pertevniyal High School in 1932. In accordance with the surname law enacted shortly before his death, he adopted the surname “Bora”.

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The subject matter of Osman Asaf Bora’s paintings derives from nature. He painted his landscapes not by studying postcards but by observing them en plein air. In this respect, he can be said to have contributed his own distinctive chromatic richness to the historical and rural landscape tradition of Hoca Ali Rıza’s generation. The landscapes he painted of Istanbul’s natural surroundings constitute his most important works. In these paintings, the artist meticulously depicted neighborhoods of Istanbul such as Erenköy, Kızıltoprak, Acıbadem, Dudullu, Kalamış, Fenerbahçe, Maltepe, Kağıthane, and Göksu streams. He also included old mansions, tree-lined roads, and cliffs in his works. Figures are rarely present in the narrow streets he typically painted. Some of his paintings feature barren seascapes or rural vistas. In rural settings, nature extends into boundless space, while elements such as trees, vegetation, and rocky formations reflect the rich texture of the environment. Among the historical structures depicted in his works are familiar architectural elements of the community such as mosques, tombs, fountains, ruins, bridges, mansions, and the Maiden’s Tower, alongside Islamic religious motifs.

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In his works, he primarily employed yellow tones, along with blue, purple, and brown tones.

In his compositions, he employed light and shadow to reveal the three-dimensional structure of objects. In paintings where the depiction of atmospheric changes was essential, he included elements such as mountains, forests, seas, and sailing vessels in the background. In his early works, he favored the oil painting technique. Due to health issues, in his later works he turned to gouache and watercolor techniques, which are less pungent than oil paint and are mixed with water. His oil paintings are nearly as finely layered as his watercolor works. He used colors cleanly, without excessive blending, and emphasized light and shadow effects. Although each of the techniques he employed holds its own distinct value, his watercolor works demonstrate a unique mastery. In addition to landscapes, he also produced a number of still lifes and figure studies, though fewer in number. In these works, his ability to evaluate objects is grounded in line and value contrasts.