"Yes, fellow tomboys — this feature is for you. From tried-and-true tropes, like Annie Hall, to a few more modern and unexpected dude inspirations, here are a few versions of tomboy style out there — and the perfect outfits to get you the look"
Military Spiffy — The army jacket may be a tomboy's most beloved piece of outerwear, so really go for it with a few other sharp, tailored pieces. The key is to make sure the fit is still slim, lest you want to end up looking like a newly enlisted Charlie Chaplin.
Tinseltown Tomboy — Annie Hall, this one's for you! We can't do a tomboy story without referencing one of our favorite icons. Do it up modern style with patterned oxfords, thick-rimmed sunglasses, and a slim-fit vest.
Bowery Punk — Leopard, leather, and studs = perennial punk staples. Creepers also can help give you a little height (since heels will probably never fit into your arsenal).
Off-Hours Mogul — Part Pharrell, part Angel Haze, this look screams Boss Lady without getting all stuffy.
Grown-Up Schoolboy — While you might not have thought florals were your thing, they very well could be on a spiffy varsity jacket like this one. Cropped pants, slick loafers, and a backpack keep that Billy Elliot-vibe alive.
Trad Dandy — Take your suits out of the office by finding one in a cropped, shrunken fit. A little silk bandanna looks cheeky tied as an ascot under a button-up (and take this as an opportunity to grow your loafer collection — we give you permission!).