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Elana in two of her fit-and-flare favorites, from MSGM (left) and Carven (right).
"I did ballet from the time I was five or so up until my later teenage years, and I definitely think that had an impact on how I dressed. To this day, I'm obsessed with the ballerina-off-duty look—a leotard or loose-fitting sweatshirt, a wrap skirt, tights and flats. But the circle skirts I wear every day are infinitely comfier and less cumbersome than tutus, I'll say that much!"
"I've always loved really feminine clothes, but definitely wore jeans all the time while growing up. It wasn't until my last few years of college that I realized that A-line skirts and fit-and-flare silhouettes really just looked and felt better on my body."
"Carven makes some of the absolute best nipped-waist, bell-skirted ones right now."

"I have a very 'in-and-out' physique—small waist, but with hips—and something that's nipped in where I'm more narrower is just so much more flattering (not to mention comfortable) than a pair of pants that are cut straight up and down."

American Apparel's another great source for skirts—I lived in their chambray fit-and-flare all through college, and now they've done a pleated version in faux silk that I love."

"So many of my personal style idols, like Sofia Coppola and Taylor Swift, wear dresses far more often than they do denim. 3.1 Phillip Lim makes really beautiful tulip skirts that transition well from work to evening."
"By the time I turned 21, I pretty much wore skirts and dresses exclusively—even during the winter, when it's freezing here in NYC. Thank goodness for black opaque tights and knee-high boots! When I was in high school, I absolutely hated our uniforms—but years later, having my own personal dress code of sorts makes getting ready every day so much easier."