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Fashion Icon: Diane Keaton
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items Diane Keaton is a true style icon whose fashion legacy spans decades, defined by confident tailoring, effortless layering, and a signature blend of menswear and femininity. From Annie Hall to Manhattan and Something’s Gotta Give, her looks prove that...
The Oliver Peoples glasses she wore became an extension of her signature style—intellectual, effortless, and timeless, perfectly capturing the confidence and individuality that define Diane Keaton’s iconic look.
Vintage Oliver Peoples Eyeglasses 45-21-145 Op-593 Gold Rimless
She would wear a grey oversized blazer with relaxed confidence—slightly slouched, sleeves pushed up, layered over crisp basics, making structure feel effortless and entirely her own.
Single-Breasted Wool-Blend Blazer
Diane would wear a long menswear-inspired wool coat with quiet authority—tailored yet relaxed, draped effortlessly over her frame, turning borrowed-from-the-boys structure into unmistakable signature style.
Jane Long Coat - Grey Melange
Diane would wear a suit vest when she wants tailoring to feel personal—layered over a crisp shirt, confident, relaxed, and effortlessly cool.
Women's Suiting Vest
Diane would reach for a tie when leaning fully into her androgynous edge—most famously in Annie Hall and Manhattan, where she styled it with tailored trousers and blazers, turning classic menswear into an iconic expression of confidence and individua...
Classic necktie - Women | MANGO USA
Diane wore a bowler hat with effortless nonchalance—most memorably in Annie Hall—and in doing so transformed a traditionally masculine accessory into something undeniably cool, proving that confidence, not convention, defines style.
Wickford
Diane would wear a button-down shirt anytime she wanted simplicity to feel intentional—crisp but slightly undone, often borrowed from menswear and styled with tailored trousers or layered pieces, making ease look effortlessly cool.
White Carolina Button Down
Diane would have enjoyed a Gigi Pip hat as a modern signature—styled with relaxed tailoring and clean lines, adding a confident, fashion-forward edge that feels intentional, timeless, and distinctly her own.
Rue Open Crown Hat
Another chic hat option that quietly whispers Diane Keaton cool.
Wool Classic
Diane Keaton would wear a suit vest layered over a slim turtleneck or a crisp collared shirt, as seen in Annie Hall, where her effortless approach to menswear made structured pieces feel personal, modern, and undeniably chic.
Hunter Green Tweed Herringbone Thompson Vest
A pinstripe collared shirt was quintessentially her vibe—sharp yet relaxed, borrowed from menswear and worn with the kind of ease that made intellect, confidence, and style feel inseparable.
Pacific Stripe Wexler Cotton Button Down
Diane’s love of menswear reshaped her wardrobe, with blazers becoming a true game changer—introducing structure, confidence, and a signature ease that transformed traditional tailoring into an iconic expression of personal style.
Generation Blazer
This silk scarf is perfect for a pop of color without being overly feminine, perfectly aligning with her neutral color palette.
Logo Equestrian-Print Silk Square Scarf
Diane Keaton’s collaboration to create the Keaton Readers perfectly reflects her signature style—bold, intellectual eyewear designed to feel timeless, expressive, and unapologetically individual, just like the woman herself.
Keaton Readers
She wore the La Reale triangle scarf as an effortless finishing touch—draped loosely around her neck during her Annie Hall era—cementing it as a symbol of her relaxed, intellectual approach to menswear-inspired style.
La Reale triangle
Diane Keaton would wear a turtleneck as a quiet foundation piece—sleek, understated, and layered beneath tailoring to let simplicity and confidence do all the talking.
RUMER FITTED CASHMERE TURTLENECK
Diane would wear a long plaid car coat with effortless ease, layered over tailored separates and worn slightly oversized so the classic pattern feels relaxed, confident, and unmistakably her.
Pressed Plaid Wool-Blend Car Coat
A blouse with a bow is a perfect option for dressing like Diane Keaton, adding a soft, feminine counterpoint to tailored pieces while still feeling thoughtful, polished, and unmistakably classic.
Santana Shirt
Diane's signature tinted lip balm in Lovely Mocha—a natural hue she gravitated towards.
Loreal Colour Riche Glossy Balm
Diane's makeup artist revealed she had preferred Rhianna's eyeliner in black.
Flyliner Longwear Liquid Eyeliner - Fenty Beauty by Rihanna | Sephora
Diane Keaton’s candle collaboration reflects her understated elegance, blending warm notes of woods, soft spice, and subtle citrus to create a scent that feels intellectual, cozy, and quietly luxurious—much like her personal style.
Diane Keaton x Hudson Grace HOUSE Scented Candle: A Signature Scent - Hudson Grace
Her first fashion book offers an intimate look at Diane Keaton’s personal style, celebrating decades of menswear-inspired dressing, individuality, and the confidence to wear exactly what feels true.
Rizzoli Fashion First In Diane Keaton
A long taffeta skirt is a great choice for dressing in Diane’s style because it adds structure and drama while still feeling intentional and unfussy, pairing beautifully with menswear pieces to balance femininity with confidence.
Max Mara Long Taffeta Skirt
The black onyx necklace she wears in Something’s Gotta Give is a subtle but powerful detail, grounding her soft, neutral wardrobe with a touch of depth and quiet sophistication that feels unmistakably Diane.
Solid Black Onyx Necklace, Black Lariat, Diane Keaton Somethings Gotta Give, Unique Black Beaded Choker Collar Necklace
Her everyday Keaton wine glasses reflect her signature sensibility—classic, unfussy, and thoughtfully designed to make simple moments feel personal and quietly refined.
"Keaton" Everyday Wine Glass by Diane Keaton x Hudson Grace - Hudson Grace
Diane Keaton’s collaboration with Hudson Grace on a plaid throw captures her love of classic patterns and cozy elegance, creating a timeless piece that feels warm, thoughtful, and effortlessly lived-in.
Diane Keaton x Hudson Grace Black & Red Plaid Alpaca Throw Blanket - Hudson Grace
Her Reggie cast iron dog door stopper is especially meaningful, named after her beloved dog Reggie—a quiet tribute to how deeply she loved him and her tendency to turn everyday objects into personal keepsakes.
Diane Keaton + Hudson Grace “Reggie” Cast Iron Dog Door Stopper - Hudson Grace