‘I wanted the clothes to make the woman’: Diane Keaton’s iconic fashion collection goes on sale

Neckties, cowboy boots, layers, oversize men’s jackets and a hat always perched jauntily on her head: Diane Keaton had a sense of style that was as unerring as it was eclectic and unambiguously personal and intentional.

She even moulded the wardrobe of Annie Hall — the struggling nightclub singer in a failing relationship with Woody Allen’s neurotic comedian Alvy Singer in the eponymous film, a role that would land her an Oscar — on her own. ‘I wanted the clothes to make the woman,’ she said, paraphrasing the motto of her hero Cary Grant.

‘Diane has always marched to the beat of her own drum, in the way she dresses and the way she lives,’ wrote Ralph Lauren in the foreword of Fashion First, the book that chronicled the actress’s looks over the decades.

‘Whether she's on stage accepting an award or on a sidewalk walking her dog with her kids, she's always herself. Her style is not defined by the moment. It's not about trends. It's authentic and forever.’

This same, exactingly curated approach she extended to collecting — American art, photography, objets — and decorating. Now, some of the greatest pieces she surrounded herself with will go under the hammer at Bonhams in four June sales.

The centrepiece of the series is ‘The Diane Keaton Collection: Architecture of an Icon’, held in New York on June 8, in which the outfits and objects that most defined her will be on offer — not least the Ralph Lauren houndstooth suit and overcoat she wore at the 2020 Oscars, which she also sported on the cover of Fashion First (estimated at $2,000–$3,000).

Other highlights include a Ralph Lauren polka dot tie ($100–$200) and a black bowler hat ($400–$600), which was such a recurring feature of her look, as well as the original script for Annie Hall ($2,000–$3,000) and artwork she made, such as Pair of Collages ($600–$800), or collected, including several paintings reflecting her long-standing fascination for the American West.

The other sales in the series, which run online, also feature fashion, interiors and objects that inspired her or encapsulated her career. Estimated at $300–$500, the polka‑dot skirt and belt she wore as Leah, the lonely neighbour of Michael Douglas’s Oren Little, who gets roped into looking after his granddaughter in And So It Goes, is one of the lots in ‘The Diane Keaton Collection: Tailored & Timeless’, a selection of more than 200 pieces of clothing, jewellery, hats and accessories that shaped her distinctive style (May 31–June 9).

Industrial furniture, California Hillside pottery and Native American pictorial weavings all feature in the second sale, ‘The Diane Keaton Collection: At Home with Diane’ (June 1–10). The third, ‘The Diane Keaton Collection: Chapters of an Edited Life’, will showcase the mixed-media collages and photographs she made, a selection of books from her library and memorabilia from her acting life, including scripts and letters she exchanged with other performers and directors (June 1–11).

A selection of pieces will be on show in Los Angeles (from May 5) and New York (from May 29) ahead of the sales.