Annie Hall had perfect timing. She toed the line between masculine and feminine just as the feminist movement was in full swing and women were wrestling with their role in society. The cool thing about Annie was that she was always delving into extremes. She went from sensitive to unemotional, silly to serious, strong to weak. Her clothing embodied her character, as she wore both flowy, feminine dresses and full on menswear outfits. She embodied the changes that women were going through at the time with charm and grace.

Technically, Annie Hall isn’t an actual person — she’s a character in a Woody Allen movie. That makes her influence in fashion all the more amazing. Annie Hall was the title character in the Woody Allen film of the same name. Diane Keaton, who played Annie Hall, won an Oscar for her performance in 1978. Her wardrobe in the film, primarily designed by Ralph Lauren and inspired by Keaton’s own look, contributed to the depth of her performance. Diane Keaton was so charming in this film that her look became an actual trend – it’s even inspiration for the current menswear trend that is happening today.

The Annie Hall look is characterized by long, lean lines that are created with loose slacks, long vests, white button-down shirts and ties. The loose fit creates length and a casual sophistication — isn’t that every woman’s dream?

The interesting thing about the Annie Hall look is that it works best on women who already have a boyish shape. It’s part of why the menswear fit is so much more comfortable to them – the slim cut hangs properly on the body and the heavier fabrics build form. If you are a curvy woman, it’s a bit tougher to pull off the same look, but you can make it work with a few tips from one of my recent blog posts.

What I love about the Annie Hall look is that it’s effortless when worn well. The assumption of the style is that you are true to yourself — regardless of what stage in life you may be. That is true style, and that is why Annie Hall is an icon. How do you show your true self in your personal style?