Boykin attended Fayette County High School and played for the varsity football team. In his senior year, he, along with fellow NFL Player Matt Daniels, led the football team into its first undefeated season in over 20 years but lost in the second round of the GHSA playoff. Boykin also played for the school's basketball team where he averaged 18 points and five assists per game while helping lead his team to the State Championship game where he and his team came up short.
Going into the 2012 NFL Draft, Boykin was projected as one of the best cornerback prospects. He was drafted in the fourth round of the 2012 NFL Draft by the Philadelphia Eagles. He signed a four-year contract with the team on May 11, 2012. His first season he recorded 31 total tackles, 7 passes defended, and 1 forced fumble. He saw little playing action on defense, but his 1,037 kick return yards was second in the NFC and seventh in the entire NFL. Boykin started the 2013 season with his first interception, off RedskinsquarterbackRobert Griffin III, helping the Eagles to win 33–27. He recorded his next interception in a week 5 win over the Giants where he picked offEli Manning. In a week 10 game against the Green Bay Packers who were without quarterback Aaron Rodgers, Boykin intercepted quarterback Scott Tolzien's pass in the endzone and ran it back for 76 yards. He followed up again the next week, intercepting Redskins quarterback Robert Griffin III. In a week 16 game against the Chicago Bears, Boykin intercepted Jay Cutler and ran it back 54 yards for the score. The week 17 showdown against division rival Dallas Cowboys was for the NFC East division title. Late in the fourth quarter the Cowboys marched down the field when back-up quarterback Kyle Orton threw behind his wide receiver, Miles Austin. Boykin intercepted the pass and kneed it after a short return. The interception led to the Eagles rushing the ball twice for a first down, then two kneel downs to run out the clock and seal the Eagles' divisional win at a final score of 24–22. Boykin enjoyed a breakout year in 2013 with 42 solo tackles, 5 assists, 2 forced fumbles, 16 passes defended, and 6 interceptions. For the 2014 season, Boykin had 36 solo tackles, 5 assists, 9 passes defended, and an interception.
Pittsburgh Steelers
On August 1, 2015, Boykin was traded to the Pittsburgh Steelers in exchange for a conditional 2016 5th-round pick.
Carolina Panthers
On March 28, 2016, Boykin signed a one-year contract with the Carolina Panthers. The Panthers released Boykin and two others to create roster space for six new rookie tryouts two months later.
Chicago Bears
On July 27, 2016, Boykin signed with the Chicago Bears. He was placed on the team's injured reserve list on August 3, 2016 due to a pectoral injury suffered during training camp.
