Irving Penn's Mermaid Dress (1950) is to cross the block with an $80,000-120,000 estimate at Phillips New York on October 1.
The work (numbered two of an edition of 25) shows his wife, Lisa Fonssagrives, wearing a dress by designer Marcel Rochas. The photograph was taken for Vogue in Paris.
Penn (1917-2009) was one of the most important fashion photographers of the 20th century, bringing a modernist slant to the medium that continues to influence his successors.
The record for his work was set for a photograph titled Cuzco Children (1948), which sold for $529,000 at Christie's in 2008.
Richard Avedon's Natassja Kinski and the Serpent (52 of 200) is likely to prove another highlight, with an estimate of $70,000-90,000.
Avedon (1923-2004) reacted against the formality of the fashion press, photographing his models in natural poses and in ordinary locations.
He commented on perhaps his most iconic photograph: "When you look at the photograph it all looks so easy...
"She spent two hours on a cement floor naked. The [snake] trainer would start anchoring the snake with her ankles and see where the snake would go... hoping that the snake, cause there is no talking to the snake, would creep up in a way that was beautiful."
His auction record stands at £719,000 ($1.1m) for a photograph of Dovima, one of the most famous models of the 1950s.
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