Shimon Okshteyn was born in Chernovitz, in the Ukraine, which was then part of the USSR. In 1970, he won entrance into the prestigious Odessa Art Academy. He spent the next ten years working and exhibiting across Russia before immigrating to the United States in 1980.

Okshteyn's style changed dramatically when he reached the US. He replaced his earlier style of socialist realism with the new American realism that gained popularity in the 1980s. Currently Okshteyn uses graphite and other media to produce precise, large-scale drawings of ordinary objects that have historical or personal significance. His work is included in the Museum of Fine Arts in Springfield, Massachusetts, the Whitney Museum of American Art and the Museum of Contemporary Russian Art, Niznij Novgorod, Russia.