Originally created by Levi Strauss for 19th-century railroad laborers and miners, the denim jacket is now taking on a new work frontier: the office. “The jacket has become a staple you can wear with a shirt and tie,” says Levi’s design director, Jonathan Cheung. “It creates an effortlessly cool look.” Today’s jackets are more fitted, available in colors beyond blue, and sometimes aren’t even made of denim. “You can pair dark jeans and a lighter-colored denim jacket, but guys worry it looks like a Canadian tuxedo,” says Paige Adams-Geller, founder of Paige Denim. “So we took the classic shape and expanded it with new fabrics and colors.” Here is our guide to wearing (and pairing) the right denim jacket in every situation.