Diane Keaton, photo by Getty Images
The overarching themes in fashion these days are individuality and personal expression. They can’t be forced or manufactured. Diane Keaton was the real deal.
I always admired Diane, a trailblazing style icon and constant source of personal inspiration, who consistently made my Best Dressed Lists and was the subject of many articles. Diane eschewed trends du jour and adopted a Dandy-ish style that strikes a balance between tomboyish and feminine elements. Her style was a declaration of individuality, long praised for its authenticity, humor, and grace.
“Turtlenecks are particularly underrated. Buy one. I dare you. Give one a try. Turtlenecks cushion, shield, and insulate a person from harm. If you take my advice, trust me, your head will be framed to perfection.” – Diane Keaton.
Diane Keaton in a signature look, photo by Getty Images
Diane’s effortless mix of menswear and monochromatic chic defined ageless style. Quite frankly, she became more beautiful and stylish with age. Both Diane and I have a soft spot for black turtlenecks. I agree they are the most flattering items you can have in your wardrobe.
Diane Keaton Getty Images
Diane preferred to cover up from head to toe, but instead of drowning herself in slouchy oversized clothes, she opted for well-tailored jackets and coats, and made sure she emphasized her waist. When Diane wore skirts (pencil skirts or full skirts), they were knee-length; all the better to show off her great gams!
Diane was a poster child for the idea that true personal style is rejecting trends and owning who you are, developing a signature that really works and shows you to your best advantage. Keaton’s style reflected her unique and joyful personality, making her fashion choices feel authentic and charismatic. She famously described her style as, “I am just being me, insane,” highlighting her embrace of individuality over conforming to trends.
Diane wearing a classic tux at the The Family Stone Premiere 2005
The most impressive aspect of Diane Keaton’s contribution to fashion was her championing of an individualistic, androgynous style that rejected prevailing norms, cementing her as a timeless icon. Rather than conforming to trends, she consistently dressed for herself, making menswear-inspired looks both chic and accessible for women.
Diane was a master of mixing masculine pieces like suits, ties, and vests with feminine touches like billowy skirts or pearls, and she always added her own bold and eccentric twist, most notably with her use of oversized hats, statement belts, and unique patterns. She was always associated with the bold combination of black and white.
Diane Keaton collaborates with Hudson Grace for a collection in black and white
In 2024, she teamed up with Hudson Grace for the brand’s first-ever collaboration. Featuring decor, kitchenware, and pet accessories, all done in graphic bold black and white. The line was a perfect fit for Keaton, who had an eye for interior design for years, publishing a book on the subject and sharing several of her own residences.
Diane Keaton Fashion First, published by Rizzoli
Meanwhile, I am running out to buy Diane’s book, Diane Keaton Fashion First, published by Rizzoli in 2024 with a foreword by Ralph Lauren. This book is a comprehensive exploration of Keaton’s fashion journey, from her early days in Hollywood to her current status as a style icon. It will be on many gift lists this year, and it’s a must-read for anyone interested in fashion history and personal style.
Diane Keaton, a look from Fashion First, published by Rizzoli
Diane was a rare breed in Hollywood, a true maverick who refused to bow to trends or subscribe to red carpet dress codes. She always championed her own eccentric style, wearing pants to formal awards ceremonies, bowler hats to balls, and neon colors to run errands.
Diane Keaton, signature style
Her fearless approach to fashion was truly liberating. She often incorporated quirky, playful, and daring elements, showing how to mix classics with dramatic details to create a personal statement. She frequently mixed seemingly disparate items, like a sequin suit with a beret, to create an outfit that is uniquely her own.
Diane Keaton in her last public photo, 2024, Instagram
Dressed in her signature black turtleneck, wide-leg trousers, and chunky lace-up shoes, Keaton exuded the effortless charm that defined her five-decade career. She shaped the way people think about clothes both on and off the screen.
Before Annie Hall, she already dressed in her own way, mixing thrift finds with menswear and clean shapes. In 1977, that became a cultural turning point. The film made her wardrobe part of film history and everyday fashion.
Photo credit InStyle Magazine
Through the decades, Keaton kept the same approach. Her love of black and white, the wide trousers, the turtlenecks, the statement belts, the hats. She managed to balance humor and control. Designers like Thom Browne, Ralph Lauren, The Row, and Gucci have all drawn from that language.
Diane showed that style can be consistent without being repetitive. Dressing with intention can convey more than just trying to impress.
