How Diane Keaton’s “Annie Hall” Wardrobe Changed the Way Women Dress

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Keaton’s signature aesthetic, menswear reimagined through a distinctly female lens, endured for decades. Her love of slouchy tailoring, crisp button-downs, high-waisted trousers, and layers of texture—tweed, wool, cotton, and silk—became her personal uniform. She favored clothes that allowed movement and comfort but still carried structure and polish. Even as trends came and went, her look remained constant: oversized blazers cinched at the waist, perfectly rumpled shirts, and the occasional necktie knotted with irreverent ease.

That effortless interplay between masculine rigor and feminine eccentricity helped define a generation of American style. Keaton’s preppy, tomboyish ensembles even helped catapult Ralph Lauren to fame and permitted a generation of second-wave feminists to dress for themselves. She accepted her 1978 Academy Award in a gray blazer and long skirt, her hair piled high in Edwardian splendor, solidifying the look as a cultural touchstone—a woman both composed and delightfully undone.



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