Comfortable has been the way to go, and with the onslaught of athleisure separates available, the options are endless. As a result it's easy to fall into that rut. Update your favorite cozy sweatshirt or hoodie with a similar style sweater in a knit fabric and pair with elevated pants like plaid checked trousers in a loose silhouette. Then, add modern sunglasses and a matching crossbody bag for the ultimate street-chic effect.