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VISUAL CULTURE: Sotheby’s in London will hold a sale of a selection of sought-after fashion photographs from the 20th century to the present day.

The sale, which will take place May 19, will coincide with the second edition of Photo London, a photography fair that brings together the British capital’s major museums, galleries and auction houses to celebrate photography.

Rare photographs from the likes of Richard Avedon, Helmut Newton, Irving Penn and Peter Lindbergh will be sold alongside works of modern-day photographers including Miles Aldridge and David LaChapelle.

Penn’s striking “Mouth” photograph taken for L’Oréal in 1986 portraying female lips smeared with numerous shades of lipstick will be included in the sale. This is only the third time the image has gone to auction and it is estimated to sell for up to 230,000 pounds, or $331,000 at current exchange.

Also among the highlights is “Models,” another Lindbergh photograph featuring supermodels of the Nineties, including Linda Evangelista and Christy Turlington, wearing men’s shirts and little makeup. It was a reaction to fashion photography’s fascination at the time with retouching.

The photograph, which was considered too avant-garde to be used by Vogue U.S. at the time, is estimated to sell between 60,000 to 80,000 pounds, or $86,000 to $115,000.

A portrait of Marilyn Monroe by Avedon stands out for capturing a different side of the actress and model.

“For hours she danced and sang and flirted — she did Marilyn Monroe. And then there was the inevitable drop. And when the night was over and the white wine was over and the dancing was over, she sat in the corner like a child, with everything gone. I saw her sitting quietly without expression on her face, and I walked towards her but I wouldn’t photograph her without her knowledge of it. And as I came with the camera, I saw that she was not saying no,” recalled the late Avedon of the portrait he took in his studio in 1957.

A nude black-and-white shot of a young Kate Moss taken by Albert Watson in 1993; Guy Bourdin’s daring photographs taken for French Vogue in the Eighties, and Newton’s classic black-and-white “Woman Into Man, Paris” photograph will also be going under the hammer.

Among the other photographs in the sale are the “Money Shot” by David La Chapelle and Miles Aldridge’s “The Rooms No. 2,” which was initially showcased as part of “I Only Want You to Love Me,” a solo exhibit of his work held at Somerset House in 2013.

“These works were carefully chosen for this auction and reflect the continued interest and collectability of fashion photography, an area in the market that has grown from strength to strength,” said Brandei Estes, Sotheby’s photographs specialist. “We expect these works will do extremely well and are delighted to have such a broad estimate range.”