5. Annie Hall (1977)

Diane Keaton’s portrayal of the title character in Annie Hall introduced an androgynous style that defied traditional gender norms. Her mix of vests, men’s ties, oversized blazers, and slouchy trousers sparked a menswear-inspired fashion trend for women, making tomboy chic a mainstream look. The film’s influence endures in today’s gender-fluid fashion landscape, continually inspiring designers to blur the boundaries between masculine and feminine attire. As noted by Harper’s Bazaar, Keaton’s groundbreaking wardrobe remains a touchstone for modern, unconventional style.