There’s an effortlessness to Diane Keaton’s best looks that she has cultivated during five-plus decades in the spotlight. From awards ceremonies to showbiz events, she has wowed on the red carpet in adventurous looks featuring sleek belted suits, voluminous layering, a neutral colour palette and swathes of gingham.
Keaton’s career began in the Broadway productions Hair and Play It Again, Sam in the late 1960s, with her first major film role coming in 1972’s The Godfather. The star then appeared in several films produced by Woody Allen – her former partner – from the 1970s. In the decades that followed, she was cast in big-screen hits such as Reds, The First Wives Club, Something’s Gotta Give, Father Of The Bride and Book Club.
The star, who is a mother to two adopted children, became known for her unique fashion sense in the 1977 film Annie Hall, for which she won an Oscar for Best Actress. Her character’s wardrobe featured predominantly vintage men’s clothing, including fedora hats, baggy trousers and ties. Since then, she has been considered an androgynous style icon, and some have credited her with making trousers suits a popular look for women.
Some core components thread together Keaton’s go-to outfits. The Hollywood stalwart favours black, white, grey and beige shades, and classic prints like gingham, polka dot and tartan. Additionally, the actress knows how to style a trouser suit for any occasion, is a fan of a chic turtleneck and isn’t afraid to play around with silhouette proportions. She also elevates her looks with cool accessories, frequently stepping out in oversized belts and bowler hats.
Diane Keaton’s best looks
From rocking the best tuxedos for women to showcasing some of best red carpet looks, Diane Keaton knows how to create an impression.
1. The Ralph Lauren tailored ensemble
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All eyes were on Keaton as she attended the Ralph Lauren fashion show in San Marino, California in 2022. The star stood out in a pair of black high-waisted wide-legged tailored trousers, which she styled with a white top, long-line blazer jacket and black bowler hat.
Wide leg crepe trousers from M&S
RRP: £29.50 | If you want to copy Keaton’s signature look, the first thing you’ll need is a great pair of smart black trousers. We like these wide-leg crepe trousers from M&S. Size up for a slouchy, cool look.
Merino wool turtleneck top from Cos
RRP: £45 | Next, you’ll need a classic turtleneck. Keaton’s signature starchy white shade is eye-catching but won’t work for everyone; instead, we like this versatile hue from Cos.
Wool fedora from All Saints
RRP: £79 | Where better to get a fedora than from the cool-girl brand, All Saints? This wool hat is truly all ages and will add a little edge to any outfit. Not sure how to style it? Then look to Keaton for endless inspiration.
2. The classic tartan midi skirt
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We love a classic print, and red tartan is a particularly timeless pattern. Keaton stepped out in an eye-catching midi skirt at the Hollywood Film Festival Awards Gala in Beverly Hills in 2005. She paired the eye-catching number with a black turtleneck knit, silky black gloves and classic black heels.
3. The slouchy gingham dress
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Keaton has fun playing with the proportions of her clothes. At an event in Los Angeles in 2019, the star stepped out in a slouchy black and white long-sleeved gingham midi dress that featured a voluminous skirt. She accessorised the tulip dress with a neck scarf in matching fabric, an oversized black belt and a pair of classic black boots.
4. The high-necked green polka dot dress
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If there’s one person guaranteed to rip up the sartorial rulebook at A-list parties, it’s Keaton. The actress attended a charity event in Beverly Hills in 1993 in a green and white polka dot maxi dress, which she teamed with a white beanie hat, layered long pearl necklaces and a pair of white brogues. Could she look any cooler?
5. The chic black turtleneck look
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Keaton knows that a black turtleneck is a key component of any capsule wardrobe. The actress looked chic at the Today show in New York in 2023 wearing the classic lightweight knit, along with a pair of black tailored trousers and black boots. She finished off her look with sleek locks and minimal make-up.
6. The belted white trouser suit
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Keaton wowed in white at a Los Angeles charity event in 2017. The actress looked stylish in a trouser suit, which she cinched in at the waist with an oversized belt. She finished off her sharp ensemble with a bowler hat, turtleneck top and heels.
7. The quirky metallic layered look
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Keaton is an enthusiastic fan of layering. The actress wore a black turtleneck beneath a short-sleeved metallic shift dress – in an easy styling trick for making any party dress more suitable for chilly temperatures – at the premiere of the film Love The Coopers in Los Angeles in 2015.
8. The chic silky green scarf
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While Keaton may prefer a neutral colour palette, she will add a bright shade to her ensembles on occasion. The actress elevated her all-black look for the Los Angeles screening of the film Brooklyn Laundry in 1991 with a silky green scarf. She paired the eye-catching accessory with a black leather jacket and black heeled boots.
9. The belted red leather jacket
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Keaton looked stylish on the red carpet at a gala in Los Angeles in 2003. The star wore a red leather three-quarter-length coat, which she cinched in with a skinny black belt. She paired the statement look with a black trilby hat, black leather gloves and a pair of black heeled ankle boots.
10. The slouchy wide-legged blue jeans
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Looking for the best jeans for a more relaxed look? Then take inspiration from Keaton’s wide-legged jeans. The actress exuded effortless style while out in a navy-wash pair in Los Angeles in 2019. She wore them with a white turtleneck and a brown leather coat, as well as an oversized brown belt and brown boots.
11. The Golden Globes aviator jacket
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It’s not a look for everyone but it’s one of her get-ups that we’ll always remember. Keaton pulled off one of the edgier looks in Golden Globes red carpet history when she arrived at the glamorous event in 1994 in a brown aviator-style jacket. She paired the casual piece with a yellow gingham maxi-skirt and finished off her look with a black clutch bag and black boots.
12. The classic ‘shirt and jeans’ combo
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One of Keaton’s key approaches to fashion is simplicity. At the Los Angeles premiere of the film Because I Said So in 2007, the actress looked sharp in a classic white shirt, blue slim-fit jeans and heels. She accessorised with layered black necklaces and a brown belt.
13. Owning the red carpet in elegant belted tailoring
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This look brings together two of Keaton’s go-to styles: monochrome palettes and smart tailoring. The star turned heads in this white trouser suit, cinched in with an oversized black belt at the And So It Goes film premiere in New York in 2014. She finished off the fresh look with dewy make-up and a chunky silver necklace.
14. The classic white turtleneck look
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There are few people who can make a white turtleneck look as elegant as Keaton. The actress dressed up the wardrobe basic with a relaxed navy trench coat, and pleated grey midi-skirt at a press conference for the film Book Club in Westwood, California in 2018. She accessorised with layered silver necklaces and black heeled boots.
15. The statement blue coat and grey lob
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Keaton stood out on the red carpet at the 5 Flights Up film premiere in New York in 2015. The star wowed in a leather turquoise blue three-quarter-length coat, which she wore buttoned-up. She paired it with layered silver necklaces, sheer black tights and classic black heels. We also love her sleek grey bob – one of the best bob hairstyles – which complements the eye-catching blue coat perfectly.
16. The sweeping black maxi skirt
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We love a black maxi skirt for a sophisticated evening look. Keaton turned heads in one at a film industry gala dinner held in her honour in New York in 2007. The actress paired it with a long-sleeved white shirt, an oversized black patent belt and a monochrome choker necklace. A timeless long skirt outfit idea that would still work today.
17. The cool belted coat look
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Keaton demonstrated a savvy way to give a baggy coat a dose of stylish shape at an event in Los Angeles in 2004. The star layered an eye-catching checked three-quarter-length coat over a black turtleneck jumper and black trousers – and cinched in the look with an oversized black belt. She accessorised with a black bowler hat and a black clutch bag.
18. The all-white Golden Globes look
19. The iconic black trilby hat look
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Keaton looked chic in head-to-toe monochrome at the AFI Life Achievement Award gala in Los Angeles in 2017. The star wore several of her trademark pieces – a white coat over a black turtleneck and full midi-skirt, which she belted in with an oversized black belt. She finished off the ensemble with a black bowler hat and black-heeled boots.
20. The stylish polka dot trousers
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We love a pair of printed trousers to jazz up an otherwise plain look. Keaton stepped out in a white pair emblazoned with black polka dots while running errands in Los Angeles in 2014. The star paired them with a black bowler hat, a black three-quarter-length coat and black heeled boots.
21. The sparkly trouser suit
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Keaton sparkled at the LACMA Art + Film Gala in Los Angles in 2021. The actress dazzled in a navy sequinned trouser suit, comprising of a blazer jacket and wide-legged trousers, over a buttoned-up white shirt. She accessorised with a black beret, black heeled boots and a nude lip.
22. The gingham blazer and white socks
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There is no stopping Keaton’s love of black and white gingham print. The actress wore the classic pattern on a blazer for Jimmy Kimmel Live in 2017. She paired it with a white shirt, oversized black belt and black leather midi-skirt, and accessorised with white socks and black heeled boots.
23. The classic brown leather jacket
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Keaton gave her smarter take on the classic leather jacket while out in Los Angeles in 2019. The star layered the chic brown outerwear over her trademark white turtleneck and a pair of loose black tailored trousers. She accessorised with her beloved black bowler hat.
24. The chic all-black look
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Keaton was the epitome of style in an all-black look at the Los Angeles premiere of the film Mack And Rita in 2022. The star paired a turtleneck with a voluminous midi-skirt, which she cinched in with a large belt. She finished off the look with a bowler hat and Louise Vuitton shoes.
25. The stylish leather skirt suit
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At an event in Berlin in 2017, Keaton rocked the red carpet in an all-black ensemble. The actress wore a leather jacket – belted at the waist – over a leather pencil skirt. She paired the sleek look with a beret and ankle boots, as well as a studded choker and a large silver cross necklace.
26. The statement Ralph Lauren coat
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Keaton wrapped up warm at the Ralph Lauren show during New York Fashion Week in 2023. The actress stepped out in a double-breasted grey check longline coat, which she cinched in at the waist with her trademark large black belt. She wore the head-turning outerwear over a black turtleneck and stripey grey trousers and finished off the stylish look with – you guessed it – a black bowler hat.
27. The chic beige suit
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At a charity gala in Los Angeles in 2018, Keaton mixed things up in a chic all-brown look. The star wore a tuxedo-style double-breasted blazer jacket that matched her wide-legged trousers, which she layered over a turtleneck. She finished off her look with a bowler hat and oversized belt.
28. The silky white suit
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Few people can make a trouser suit look as glamorous as Keaton. The actress stood out at the premiere of the film Mad Money in Westwood, California in 2008 in a silky white buttoned-up blazer jacket and slim-fit tailored trousers. She dressed up her look with a ruffled blouse and white heels.
29. The statement Gucci coat
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Keaton turned heads at a Gucci event in Los Angeles in 2021. The star looked stylish in a three-quarter-length coat emblazoned with the fashion brand’s signature print, which she wore over a white shirt dress. The star paired her look with a brown bowler hat, red and nude heeled boots, and a smokey eye – which is an easy make-up look for evening.
30. The cool tartan trouser suit
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We love navy tartan print, and Keaton wore the classic pattern as part of a chic trouser suit look at the premiere of Netflix’s Green Eggs And Ham in Los Angeles in 2019. The star finished off her bold ensemble with a black turtleneck, layered silver cross necklaces and chunky black ankle boots.
31. The elegant striped coat dress
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Keaton looked elegant at the premiere of the film Book Club in New York in 2023. The actress wore a stripey monochrome coat dress, which featured a voluminous skirt – enhanced by her oversized black belt at the waist. She accessorised with a black trilby hat and boots.
32. The chic grey Thom Browne look
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Keaton looked seriously stylish at the Thom Browne show during Paris Fashion Week in 2023. The star looked sharp in a cream three-piece suit – featuring subtle white stripes and a matching oversized belt. She finished off the look with a straw wide-brimmed hat and an unusual dog-shaped straw handbag. She completed the androgynous look with a feminine touch – a pair of sky-high monochrome heeled boots.
