Much like his debut album (also released in 1966), Leavin' Town features a more tempered vocal approach from Jennings and the countrypolitan production that was typical at RCA at the time. In his 2013 book Outlaws: Waylon, Willie, Kris, and the Renegades of Nashville, author Michael Striessguth notes, "One of the early hit singles, 'Anita, You're Dreaming,' co-written by Waylon and [Don] Bowman, found Waylon in a serious and cautious vocal mode that remembered Jim Reeves, only this time with a trace of Marty Robbins, whose famous Latin sound rose up on Waylon's albums more than a few times in the 1960s." In the authorized Jennings video biography Renegade Outlaw Legend, producer Chet Atkins recalled, "I was just trying to make a record that would sell that the disc jockeys would play. I never thought, 'Let's make a pop record' or "Let's make a folk record.' I didn't think too much in that direction."