Paisley, patent leather, oxblood, bright red, soft peach, and gold — when you break it down there's a lot going on in Rebecca Ramsey's ensemble. But, the sleek silhouettes (and her understated swagger) make for an overall deceptively simple look. And, sure, as the temps continue to drop, you might need to throw a leather bomber jacket over this thin silk number, but the length of the shorts, the buttoned-up top, and the closed-toed shoes transition the otherwise totally summery bottoms seamlessly into fall. Our favorite part? The season's hottest color (dark merlot) on Rebecca's bag, paired with the pop of rouge in her blouse (and lipstick!). You go, Glen Coco!