Let's face it: deep down, we all want to channel the effortless style of a rich New Yorker! Thankfully, there's no better time than fall to embrace your inner Upper East Side socialite with a host of comfy fall dresses that bring fashion and function to the forefront. Lucky for Us, Amazon has a ton of expensive-looking dresses that will have you resembling a modern-day Carrie Bradshaw. From luxe fabrics to slimming silhouettes, these 17 dresses - starting as low as $14 - evoke expensive taste without expensive price tags. 17 Comfy Dresses to Look Like a Rich New Yorker 1.