1. The Chambray Shirt — Not many pieces can boast comfort and versatility, but the trusty chambray shirt is our go-to for easy cool. Super-soft but still crisp, wear you 'bray with a suit and tie (holler, JT) or untucked over some khakis. And, if you dare, we're all for a seasonal Canadian tuxedo.

American Apparel Heavy Chambray Long Sleeve Button-Up, $60, available at American Apparel; Shipley & Halmos Button Down Clean Woven Shirt, $225, available at Shipley & Halmos.