Most of us can’t walk around dressed like Ashlee Simpson all the time (nor would we want to), but her style has evolved a bit over the years, and now that she’s expecting, she’s been seen in some pretty free-spirited but stylish stuff. This look caught our eye because it’s not your typical maternity dress and flats —instead it’s a casual/going out with friends look that’s got a little funky edge to it, but is still actually wearable. One note: the shoes, while fab, are decidedly not maternity—so be sure that wherever you’re going, you’ll have the opportunity to look smashing while sitting down . . .

Black cotton/spandex ankle length legging, $12.98, Motherhood Maternity

Lauren Kiyomo Yoko Kimono Maternity Top, $59.95. Stella Maternity

Women’s Mossimo Vernice Patent Peep Toe Pumps, $26.99, Target

Fall Fab Houndstooth Scarf, $4.50, Forever21 (and it comes in other colors, too, should the orange and black strike you as, oh, too Halloween-oriented . . . )