Ask Harriet (1998)

This sitcom with a "Tootsie" twist revolves around Jack Cody, who is so desperate for a job after being fired as a sportswriter that he applies to the same newspaper for the job of advice columnist -- as "Sylvia Coco." Unfortunately for Jack, his boss (and former girlfriend) Melissa Peters insists that "Sylvia" be available for high-profile personal appearances and staff meetings, so before you can say "cross your heart with lasting stretch," poor Jack has to don a dress, silky undies and high heels to save his new job.