At 75, Diane Keaton proves that ageless style really does exist

  • Oops!
    Something went wrong.
    Please try again later.
·4 min read
In this article:
  • Oops!
    Something went wrong.
    Please try again later.
Diane Keaton out for ice cream in Los Angeles, and on the set of Mack & Rita in Palm Springs 
Diane Keaton out for ice cream in Los Angeles, and on the set of Mack & Rita in Palm Springs

Diane Keaton: Lockdown style iconoclast? Last week, images of the Academy Award winner wearing an oversized white button-down shirt, snakeskin-look thigh-high stiletto boots and a long silver wig went viral.

That look was a costume, worn by Keaton in character on the set of Mack & Rita. Apparently it’s a Freaky Friday-ish film in which a 30-year-old woman named Mackenzie is magically transformed into Keaton’s 65-year-old Rita.

The outfit drew attention for its audacity (snakeskin stiletto boots? in a pandemic??) as much as for the woman wearing it (those legs!).

But for Keaton, 75, the look was just the latest entry in a life filled with epic outfits. She’s one of the few women who have managed to maintain and evolve a consistent style for decades. As a result, over her more than forty years in the public eye, Keaton’s all-time most stylish character has been herself.

The Diane Keaton look comes down to monochromatic menswear-inspired tailoring, directional trousers, lampshade skirts, chunky boots – and hats galore. In 2019, she started posting selfies to her Instagram feed, accompanied by all-caps captions lauding the near-magical powers of specific clothing items.

She described a picture of herself in a black hat, black polo-neck top and belted, wide-legged jeans as follows: REGARDING THESE PANTS: THIS IS SERIOUSLY TRUE. I WORE THEM ON THE PLANE. I WORE THEM IN THE HOTEL DUPONT. I WORE THEM IN THE DELAWARE ART MUSEUM. I WORE THEM ON A LONG WALK THROUGH THE WILMINGTON STREETS. I’M WEARING THEM ON THE TRAIN TO NYC. I’VE NEVER RECEIVED MORE COMPLIMENTS ON ANYTHING I’VE EVER WORN IN MY ENTIRE LIFE.

I mean, sold.

Last summer, at the height of regional lockdowns in the United States, Keaton expanded from photos into videos. In one three-minute film, she flips through an album of favourite looks. Of a quilted skirt she wore over the trousers in a Thom Browne suit, she says, “I decided I’d put a skirt over it. Because I’m insane.” After a series of monochromatic looks: “You may think that all I’m interested in is black and white. And you’d be right.”

In another video, Keaton shares her prescription against lockdown-related despair: hats. “[This is about] how the hat can help us out in these times of trouble,” she says, indicating a table of 12 bowlers, top hats, fedoras and other manner of headpieces in her preferred spectrum of cream, grey, black and brown. “As you can see, I have a problem,” she says. “I’m addicted.”

It’s all very Moira Rose, in the best possible way. And keep in mind that these are the looks she wears at home, in private. In public, she embraces the opportunity to wear more theatrical versions of the same building blocks.

For the 2020 Oscars, she wore an ensemble by Ralph Lauren: a full-length black-and-white plaid coat belted over a black-and-white houndstooth suit, plus (of course) a hat. That look recalled her 2004 Oscars outfit, also by Ralph Lauren: an evening jacket with tails, wingtip shoes, hat and tie.

It’s easy to draw a line back from these signatures to Annie Hall. As the titular character in Woody Allen’s 1977 film, Keaton played a woman based on herself (Annie is one of Keaton’s nicknames; her original surname was Hall). Annie wears mannish trousers, men’s shirts, waistcoats, bowler hats, ties and cravats. The film was an instant classic and has endured, inspiring fashion designers and modern icons from Alexa Chung to Kate Moss.

Diane Keaton and Woody Allen in Annie Hall - REX
Diane Keaton and Woody Allen in Annie Hall - REX

Staying true to her own style across the decades has ensured that Keaton always looks like herself – that steadfastness and ability to find joy through personal style has proven a virtue in the fast-changing fashion world. No wonder, then, that Gucci – a luxury fashion house that has done more than any other to elevate genderless style, and which does a strong line in tailoring and quirky hats – signed Keaton for its latest campaign.

The “Beloved” campaign, shot by filmmaker Harmony Korine, also stars Harry Styles, Sienna Miller and Serena Williams. For her portrait, Keaton wears a very Diane Keaton-esque outfit of a pink shirt, rust-red tie, camel blazer and red beret. As Diane Keaton might say in her next style video, you’re never fully dressed without a hat.

For more news, analysis and advice from The Telegraph's fashion desk, click here to sign up to get our weekly newsletter, straight to your inbox every Friday. Follow our Instagram @Telegraphfashion