Jerry Hall, the cover girl of over forty magazines since the launch of her career in the early 70’s, is auctioning off her personal art collection. The collection, which includes several portraits of herself, intimately traces the model’s life, recounting her glamorous career and her retreat to domestic comfort.

Highlights from the auction include Andy Warhol’s Dollar Sign, a present to the top model which traces back to her involvement with Warhol T.V. Bringing Warhol’s iconic style to television, Hall’s interviews on the show followed only two rules “never ask [guests] about their work and never ask them anything important.” The painting, one of Warhol’s works never before on the market, is estimated at £120,000-150,000.

Also on the auction block is work by Lucien Freud, the British artist whose autobiographical paintings often reflect his own familiarity and sensual understanding of his subjects. Late into her fourth pregnancy, Jerry Hall started sitting for Freud, an experience that, in her own words was “a great gift” given her condition. She found it “so exhilarating to be appreciated for being natural and hugely pregnant,” yet the painting emits the tranquil acceptance of the expectant mother. Titled Eight Months Gone, its soft palette suggests an almost timeless tradition. The piece should fetch £300,000 to 400,000. Other works by Lucien Freud that will be featured in the upcoming auction include Quinces, valued at £150,000 to 200,000, and a sketch of Four Figures, well worth its estimated value of £6,000 to 8,000.

Certainly reflective of a generation, Hall’s collection also includes the Head of Helen Gillespie, finished by Frank Auerbach in 1965. Auerbach, a close contemporary of Lucien Freud, is known for his need to have a pre-existing familiarity with his subjects, one which allows him the freedom of “artistic interrogation.” This piece, one of the artist’s early works, still maintains Auerbach’s intense energy and preserves the layering of mood and image for which he is so well known. Perhaps one of his best works, the painting is expected to fetch £700,000 to 900,000.

Part of Sotheby’s Contemporary Art Sale, Jerry Hall’s collection will be offered on October 15th and 16th.