[2] After redshirting his freshman year, he contributed to the Badgers' defensive unit in 2017, playing 11 games and helping the team achieve a 13-1 record and an Orange Bowl victory.

Loudermilk was a member of the team that went to the Big Ten championship game in 2019 where the Badgers lost to the Penn State Nittany Lions.

In 2020, he earned All-Big Ten third-team honors and finished his college career appeared in 40 games, finishing with 63 tackles, 10.5 tackles for loss, and 7.5 sacks[4] Loudermilk was drafted by the Pittsburgh Steelers in the fifth round, 156th overall, of the 2021 NFL draft.

[8] The Steelers faced significant injuries to starters Stephon Tuitt and Tyson Alualu, which opened opportunities for Loudermilk.

[9][10] In the 2022 season, Loudermilk played in 11 games, recording 8 combined tackles (4 solo and 4 assisted) and no sacks.