Kenny Pickett attended Ocean Township High School in Oakhurst, New Jersey. He led the Ocean Township Spartans to the New Jersey Central Group III semifinal game as a junior, leading his team to a 9-2 record. During his high school career, Kenny Pickett passed for 4,670 yards with 43 touchdowns and rushed for 873 yards and 17 touchdowns. Upon completion of high school, Pickett originally committed to play college football at Temple University, but later changed the commitment to the University of Pittsburgh.
Kenny Pickett appeared in 52 games for the Panthers over five seasons. In those 52 contests, Pickett totaled 12,303 passing yards on 1,674 career pass attempts. He completed 1,045 of those attempts (62.4%), and threw 81 touchdown passes in his college career. In addition to the work with his arm, Pickett totaled 801 yards with 21 touchdowns on 417 career rushing attempts. His best season came in his 2021 senior season in which he threw for 4,319 yards and 42 touchdowns along with 233 yards and 5 more scores on the ground.