He played college football for the Eastern Michigan Eagles and went undrafted in 2017, having short stints with the Indianapolis Colts, Cleveland Browns, and Los Angeles Chargers before signing with the Kansas City Chiefs, where he won Super Bowl LIV and LVII.

[3] Wylie signed with the Kansas City Chiefs the next day and was promoted to the active roster on January 8, 2018.

At the end of the season the Chiefs gave Wylie the 2018 Mack Lee Hill Award as the team's best first-year player.

[11] Wylie started the Chiefs' first two games of the postseason at right guard, but was shifted to right tackle for Kansas City's loss to the Tampa Bay Buccaneers in Super Bowl LV after starting tackle Eric Fisher tore his achilles in the AFC Championship Game.

[15] His performance in the 2022 regular season was criticized for his inconsistency due to surrendering 49 pressures and allowing nine sacks.

[16][17] Wylie started Super Bowl LVII and was part of an offensive line that gave up zero sacks against a vaunted Philadelphia Eagles defense, as the Chiefs won the game 38-35.