It all started with Diane Keaton in Woody Allen’s 1977 film, Annie Hall. She was beautiful, interesting, sexy – and wearing men’s clothing. A collective fashion gasp was heard around the country.
Taking her cue from the burgeoning women’s lib movement, Keaton’s character didn’t just accessorize with a men’s-style piece or two – she wore it all. Blazers, baggy pants, vests, oversized shirts, ties, and floppy hats. Men’s fashion on women became as much a political statement as a fashion direction. Men’s clothing was inherently more comfortable than women’s, and women took a cue from Annie Hall and began experimenting with the addition of a jacket, vest or tie to their more traditional outfits.

 

It was in the early ‘80’s that this look really started taking off. New Romantic girls dressed in men’s shirts and skinny leather ties, topped men’s vests with ornate brooches at the neck, and sported stylish fedora hats. Amy Linker, who played the eternal outcast Lauren Hutchinson on the ‘80’s hit TV show Square Pegs, liked to wear suspenders – and Square Pegs fans followed suit. The masculine look was often offset with more feminine accessories, such as the Cyndi Lauper-style bangle bracelets.

 

The opening of men’s closets to girls gave them a much broader range of fashion options to choose from. Ironically, it never worked the other way – there hasn’t yet been a major fashion trend where men started wearing skirts and dresses. It’s just as well – we’re sure they’ve figured out that wingtips are far more comfortable than 3-inch heels anyway.