Bailey starred at Miramar High, where he was teammates with Geno Smith, and was coached by former Mountaineer Damon Cogdell. Bailey caught 68 passes for 1,163 yards and 14 touchdowns as a senior. He was a Florida Class 6A first team all-state selection as a senior and second team as a junior.
Bailey redshirted his first year on campus. In 2010, as a redshirt freshman, he played in all 13 games, and recorded nine starts. He caught 24 passes for 317 yards and four touchdowns. In 2011, Bailey hauled in 72 passes for 1,279 yards and 12 touchdowns. He was named to the All-Big East second-team by the conference's coaches. Bailey had his biggest season yet in 2012. Bailey caught 113 passes for 1,627 yards and 25 touchdowns. He set a school record for consecutive 100-yard receiving games (five), against Maryland, LSU, Bowling Green, UConn and Syracuse. Bailey became one of three players to finish with more than 100 yards receiving at Maryland, the first time three players netted at least 100 yards on catches in WVU history and the first time since 1998 WVU had multiple 100-yard receivers. Bailey was named as a second-team AP All-American.
Extremely productive. Showcases tremendous physicality in his routes. Uses his hands and body to create separation. Excellent body control. Very reliable target, volume catcher. Soft hands, can make plays off of his frame. Smart receiver who is adept at finds holes and picking up the first down. Tracks the football well over his shoulder and adjusts his body in order to make difficult catches. Competitive.