All of Diane Keaton’s looks that explain why she was a fashion icon for over 50 years

The era of red carpets filled with fashion brands with duly rewarded commercial interests and celebrities who sign lucrative lifetime contracts to represent the style associated with a particular brand has distorted the concept of the “fashion icon.” In 2025, a fashion or style icon may be someone who always attends the front rows of the most important fashion shows, who manages to faithfully and skillfully follow the prevailing trends, or who is chosen for their fame as a representative of a brand's values. None of that was Diane Keaton, who burst onto the scene in the mid-1970s as a woman who defied the prevailing codes, created her own trends, and had a personal, unique, and non-transferable idea of what a wardrobe should be. She was all of those things until the end of her life. In the picture, she is seen strolling through New York in a sky blue Adidas tracksuit and a long-sleeved Ralph Lauren undershirt. TPLP (Getty Images)

Although she had already starred in a box office hit such as ‘The Godfather’ in 1972, Diane Keaton became a global star in 1977, the year she starred in ‘Annie Hall’, directed by Woody Allen, for which she won her first Oscar (she ultimately won four), as well as a BAFTA and a Golden Globe. All the clothing in the film was designed by costume designer Ruth Morley; however, if Keaton's character's style was so close to what the actress herself wore off-screen, it was because there was a lot of herself in it. Many of the clothes she wore were hers in real life, and Morley took advice from this woman who already had a very particular idea about fashion.Bettmann (Bettmann Archive)

Keaton dared to boldly reclaim oversized men's clothing and outdated items such as vests, clunky shoes, and “ugly” ties. It was unusual for chic women to rummage through boxes of used clothing, also known more euphemistically as “vintage” (that was more the domain of rockers and bohemian underground types), and she did so with an artistry that set a trend. In the image, in one of the scenes from Annie Hall, she appears wearing a lingerie T-shirt as an outer garment. This was also unusual at the time. United Artists (Getty Images)

She attended the ceremony wearing a white suit by Australian designer Richard Tyler, who at the time was a favorite among Hollywood stars looking for impeccably tailored, extravagant clothing. Tyler, an independent designer, was known in Los Angeles for his ability to create stunning evening gowns and impressive tuxedos. For Keaton, who was his personal friend, he made something halfway between the two (Tyler, who also regularly dressed Julia Roberts, is still alive but the shine on his business has long since faded).Fotos International (Getty Images)

A year ago, the actress participated in a book titled Fashion First, published by Rizzoli and produced in collaboration with Ralph Lauren, in which she offered her views on fashion and discussed her own style choices, including her 1978 Oscar look. In it, she spoke about the recently deceased Giorgio Armani and her own mistake that night: "Giorgio dressed me in a look that honored my love of blazers and layers and even managed to remind me how much I love skirts. However, the decision to wear leggings... I think, now that I see them with the benefit of hindsight, that they were a little too eighties." Bettmann (Bettmann Archive)

Keaton became a desirable subject for paparazzi looking for stylish stars (Ron Galella made entire albums of her outings on the streets of New York). When she appeared alongside Woody Allen, it was clear how much her real personality resembled the archetype the director had created for her. As the filmmaker said in the obituary he published after the death of his brief partner and then friend for many years of his life: “Whether she was criticizing one of my films or a play by Shakespeare, she held them to the same standards. She had complete confidence in her own aesthetic judgment.”Art Zelin (Getty Images)

One of her most talked-about relationships in her early years of success was with Warren Beatty, with whom she began a romance during the filming of Reds, in which they both starred and he was also the director. Keaton's image in those years was still far from the archetype of the sex bomb attributed to many actresses of her age and level of success. She did not renounce an intellectualized, bohemian, comfortable, and slightly masculine view of clothing. Images Press (Getty Images)

And in this image, walking through the streets of New York in 1981 with Beatty (they were together for five years and remained friends throughout their lives), we can already see another of the distinctive elements of the ‘Keaton look’ (along with waistcoats and pleated trousers): the bowler hat. This type of hat accompanied her throughout her life. On more than one occasion, she explained that her love of hats stemmed from her aversion to sunlight, which could damage her skin, as she had a chronic skin condition. In any case, she also wore them at night.Art Zelin (Getty Images)

Having on-again, off-again relationships was something that suited the actress, because she also followed that pattern with Al Pacino, whom she met on the set of ‘The Godfather’ and whom she began dating with each new installment. It was after the last one that she gave him an ultimatum: either marriage or hit the road. Pacino chose option B. In the picture, we can see them together at the premiere party for Scent of a Woman. She is wearing her signature bowler hat and one of the elements that would become part of her most characteristic looks from the 1990s onwards: crucifixes hanging from a cord. Ron Galella, Ltd. (Ron Galella Collection via Getty)

Following her role as the executive in ‘Working Girl’, the 1989 film that explored the challenges of motherhood for women pursuing careers in finance, to the first half of the 1990s, Keaton seemed to embrace the ‘First Lady look’ (jacket suits with pencil skirts, sensible pumps, impeccable symmetrical haircuts, bangs, sheer stockings) that would reach its peak with ‘The First Wives Club’, the 1996 film she starred in alongside Goldie Hawn and Bette Midler, which cemented her place in the popular imagination as the epitome of the sexy mature woman. Jeff Kravitz (FilmMagic, Inc)

However, nothing could dissuade Keaton from her pet subject: clothing as a manifesto for comfort, that very masculine privilege. At the 1995 Cannes Film Festival, she made her directorial debut with ‘Unstrung Heroes’ and showed up at the premiere dressed like the legend she was. A black suit with satin lapels, a bow tie, a red handkerchief in her lapel and, of course, the flat shoes that were always her trademark. Glasses, both prescription and for the sun, were one of the accessories the actress often used to make fashion statements.Stephane Cardinale - Corbis (Corbis via Getty Images)

Although she had already demonstrated in 1977 that the white men's suit was her specialty (as it had also been Bianca Jagger's), in the second half of the 1990s and into the new millennium, it became her signature color. She used to alternate it with black capes or, as we see in this image taken at the 1997 Oscars alongside her friend Steve Martin, as a complete look. Keaton often wore gloves to protect her hands from the sun. Bob Riha Jr (Getty Images)

In 2017, we saw her at the tribute to ‘The Godfather’ held at the Tribeca Film Festival, showing off her collection of crucifixes, which she never wore for strictly religious reasons, as she explained, but rather for artistic and “spiritual” ones. Total black looks also defined the wardrobe of a woman who could never have been described as mournful, solemn, sober, or sad, even though her color palette very rarely included bright colors.Kevin Mazur (Getty Images for Tribeca Film Fe)

In 2021, she was one of the women chosen by Alessandro Michele to be part of the cast of celebrities who attended the gala held by the Los Angeles Museum of Contemporary Art in collaboration with Gucci. She attended wearing a spectacular sequined dress with the Florentine brand's logo subtly embroidered on it. On her head, this time, she wore a beret, another of her favorite headpieces.Taylor Hill (WireImage)

In the last decade, her direct link with the fashion industry had been rekindled: Ralph Lauren had begun inviting her to all the firm's fashion shows at the turn of the century and giving her a prominent role in them and others, while Thom Browne granted her super VIP status. In the picture, we can see her at this American designer's fashion show in Paris two years ago. It is not easy to find a star who embodies the spirit of fashion and is a style icon simply because it is one of their innate qualities. Diane Keaton was one of those stars. Pierre Suu (Getty Images)