In the course booklet of style, menswear dressing is an advanced-level class. Unlike doing the whole tomboy-femme thing, it requires a lot more thought than just throwing on one or two "borrowed from the boys" pieces because, really, it’s not borrowing at all—it’s straight-up stealing. You’ve got to know what you’re doing before committing to that.
That said, making layers of sports coats, ties, suspenders and tweedy trousers look good is difficult, but definitely not impossible. Don’t let the challenge freak you out! As you’ll see from the street style stars in the slideshow above—all prime examples of how women should wear suiting—a great Annie Hall outfit is worth all that extra effort. I’ve made it a little easier on you, too, by breaking down each lady’s ensemble, and shopping out its key piece online. Click through for 11 menswear looks you can count on.