There’s a fine line that we must walk when we want to feel comfortable in our clothes without looking too loosely thrown together. This New Yorker has the formula down. Safe to say, a chambray shirt is key. When you pair it with a luxe piece—anything from a dramatic maxi dress to a pair of silky slouchy pants—the higher end item still looks great, but it feels just a little more laid back. After that, it’s all about the accessories. Here, classic jet-set pieces like a Michael Kors watch and aviator sunglasses bump it up, while unexpected orange sandals keep it young and playful.