In my mind, there’s nothing more stylish than a woman dressed in “men's” clothes.
Pants, ties, tweed blazers, brimmed hats, leather boots... It seems crazy now to think that pants didn’t become a mainstay (or even a component) in a woman’s wardrobe until the late 19th century. Women also pillaged their husbands closet for pants when they entered the workforce while “the men were away” during World War II. It wasn’t really until the 1970s that pants were thought to be “fashionable” though *(there are definitely early style icons such as Katharine Hepburn, Coco Chanel, and Marlene Dietrich who rocked menswear in the 1930s).
A couple of my favorite websites that focus on women rocking ”menswear” and the tomboy look are Wearing The Pants and Tomboy Style. Both are a great source of inspiration if you’ve been wanting to infuse your wardrobe with some boyish flair. Wearing The Pants is a Tumblr that boasts over a year’s worth of archived photos to gobble up and Tomboy Style is a blog run by the lovely Lizzie Garrett (author of the popular new book by the same name!) featuring short interviews with creative women, vintage photos of stylish tomboys with links to clothing so you can “get that look,” and just basically everything your little tomboy-heart desires from a style-site.
I like how Lizzie Garrett describes the tomboy look on her site: “To define a tomboy requires far beyond the simple notion of wearing boys’ clothing. Tomboys have influenced the expanses of popular culture including fashion, film, music and literature. And although the tomboy is often identified by clothing, what makes her wholly so is an inherent sense of confidence, rebelliousness, and adventure.” Well put Lizzie.
I’ve also started a Pinterest board titled “Keep it Classic” with over a hundred pins of my favorite vintage-y menswear looks. Below are some of my favorite images from these three links.