Why it works: You already know how versatile it is. The trick is to make this wardrobe workhorse feel a little more thoroughbred. Look for of-the-moment details: a band collar, zippers instead of metal buttons. Then, for a pleasing contrast, pair it with silky floral shorts and saunter into the winner's circle.
Jacket, 3×1, $395, intermixonline.com; Tee, 6397, $165, shopbop.com; Bag, Marc by Marc Jacobs, $98, bloomingdales.com; Sunglasses, Illesteva, $280, illesteva.com; Silk-cotton, J. Crew, $148, jcrew.com; Sandals, Circus by Sam Edelman, $45; at Lord & TaylorRead MoreLess