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Classic Ballet Flats:

Their tasteful, pretty shape goes with everything, says Anne Keane. Above, they de-sexy-ify a slim striped miniskirt. “Imagine that skirt with wedges or heels,” says Anne. “You’d look trashy. The ballet flats make it demure and cute.” The skinny-skinny jeans above would swerve quickly into Real Housewives territory if paired with heels (nude platform pumps, I’m talking to you!). With ballet flats, however, they are super-adorable Natalie Portman material. We’ve shown the jeans worn longish, but they’d look just as cute cropped, btw.

 

Lace-Up Oxfords:

They’re tomboy where the ballet is more girly. So: Embrace the boyishness—cropped, not-tight trousers are perfection. Look at pictures from any Thom Browne show, and you’ll get the idea. “The key is your ankles showing,” says Anne. “If the pants were touching the shoes, you’d just look like … a man.”
The other option is to contrast the boyishness with flouncy femininity—in this case (above), a poufy floral skirt. You could also do long and flowy, Anne notes: “Either way, it’s about juxtaposing the boy with the ‘Hey, I’m a girl!’ ”

 

Slipper Flats:

“So great!” exclaims Anne. “It’s like this old-lady-hipster vibe, and then kind of Lord Grantham.” Wear them with boyfriend jeans for a louche/casual look or, as with oxfords, girl it up. “This fit-and-flare skirt [right] is perfect; an A-line would work, too,” says Anne, who warns that longer skirts do not work here: “That would be nerdy-nerdy, not ironic-nerdy.”