Dear Lucky: How Do I Wear Flats, Oxfords and Low Heels?

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.