The Academy had a long standing rule that required an artist to submit an original work and a self portrait in their application for membership and Singer Sargent submitted an original portrait of Claude Monet and his own Self Portrait 1892 work. His application for membership was successful and Self Portrait 1892, along with the self portraits of many prominent American artists, has been in the Academy's possession ever since. Self Portrait 1892 measures 21" x 17" and while John Singer Sargent was known to also use watercolours and produce charcoal sketches and drawings, Self Portrait 1892 is an oil on canvas. This was in line with the fashion of the time and while alive, Singer Sargent was very much a fashionable artist.

Over the course of his life, Singer Sargent produced other self portraits, but Self Portrait 1892 is well regarded for its realism and is considered an excellent example of the artist's particular skill with brushwork. In the painting, Singer Sargent is dressed in the formal Edwardian fashion of the day, in a dark frock coat, winged collar and silver necktie. But the remarkable thing about Self Portrait 1892 is the artist's portrayal of his own face. Singer Sargent has a slightly askew posture. The left side of his face is shadowed whereas the right side is well lit. The effect is pleasing and the facial detail is remarkable. Possessing a full head of dark hair, a luxuriant moustache and a trimmed beard, John Singer Sargent would have been in his mid thirties at the time of producing Self Portrait 1892 and his face shows a confident man in good health.

In later years, particularly after Singer Sargent's death in 1925 and the emergence of more contemporary schools of painting, works such as Self Portrait 1892 and American portraiture artists from this era in general fell out of favour. Because many of these artists painted for rich and fashionable society figures, they came to be seen as superficial and gauche. But artists such as Singer Sargent were rediscovered by collectors and critics later in the 20th century and works like Self Portrait 1892 are now considered excellent examples of the realism school from the Edwardian era. John Singer Sargent is now a highly regarded and highly collectable American artist.