Every Chicagoan knows all too well the heartbreak that comes with packing up your summer favorites to be worn in cooler climes. Goodbyes are hard. This year, though, stop the sulking by perusing our collection of spring and summer dresses you can totally pull off in Chicago's notoriously cooler temps. By changing up what you wear over and under these versatile frocks, you'll basically double your wardrobe. A cool, neutral dress leaves your accessories window wide open. Break out your thinking caps (and your fall accessories), and get more life out of your clothes than you ever thought possible. A classic pair of boots, a great pair of leggings, or a layer or two might be all you need to make sure you never, ever have to say bye-bye.