In a city with weather as predictably unpredictable as Chicago’s, versatility is essential. Give your look dimension (while adding noncommittal warmth) by layering fitted denim under a second, light layer. This jacket from Bleulab ($165), available at The Blues Jean Bar (2210 N. Halsted St.; 773-248-5326, thebluesjeanbar.com), is a model of flexibility. The all-denim piece is reversible—with a dark blue wash on one side and a resin finish on the other. Button a sophisticated cotton jacket—such as the washed-out army-green Harlow jacket by Joie ($253, not pictured), available at Trillium (1744 W. Division St.; 773-698-8162, trilliumchicago.com)—over the denim, pull up your collar, and dare the temperature to snap.
Photography: Heiji Choy Black and courtesy of vendors