Yangchen Lhamo, 34: Call this dress (Ann Taylor, $160) the Michelle Obama shift, after the refined-yet-stylish sleeveless versions the First Lady favors. It's above the knee but not mini-length. And an animal print in black and gray is tamer than orange tiger stripes or cheetah spots—and thus more wearable, even to the office. Mix with luxuriously textured accessories: a croc-embossed belt (Terry Stack), oversize clutch (Gucci), pearl necklace (M.C.L. by Matthew Campbell Laurenza), and leather and mesh heels (Giuseppe Zanotti Design). Ring, David Yurman.
Kelley Lauren Hicks, 24: The younger you are, the more leg you can show. In its 20-something incarnation, the shift has been drastically shortened. Worn over black leggings (American Apparel, $26) and zipped up with a leather motorcycle jacket (Etiqueta Negra, $1,200) and Jimmy Choo zebra-stripe flats, it's unexpectedly fierce. Asked if she ever thought she'd be wearing Ann Taylor, Hicks, a retail supervisor, said, "No—I'd think my mother would!" Turns out they both can. Necklace, Janis by Janis Savitt. Bag, Kooba.
Elena Agostinis, 57: The same dress goes with a lined-to-match swing jacket (Ann Taylor, $225), which makes the outfit more age appropriate, as do the opaque tights (Hue). "Animal prints remind me of home," says Agostinis, who's originally from South Africa and describes herself as "a very extroverted dresser." Accessories in hunter green—fall's new neutral—include a lizard belt (Kara Ross) and knee-high suede boots (Manolo Blahnik). Necklace, Isharya.