While attending Juilliard, Alvarez trained at the Chautauqua Theater Company, appearing as Bernard in Death of a Salesman and Puck in A Midsummer Night's Dream in 2008. Alvarez portrayed the titular character in Brain Trust Production's The Tragedie of Cardenio at the 2010 Midtown International Theatre Festival, for which he won the award for Outstanding Lead Actor in a Play. After graduating from school, Alvarez performed in regional theater, landing his first professional acting role in a national tour production of Ramona Quimby, based on the popular children's book series. He continued to perform in regional theater, cast in a production of Julius Caesar as Lucius and Metellus Cimber and in Measure for Measure as Claudio for the 2011 Oregon Shakespeare Festival. His performances at the Oregon Shakespeare Festival resulted in his recruitment to Asolo Repertory Theatre, where he received praise for his lead role of Hamlet in the theatre's production of Hamlet: Prince of Cuba, a Spanish and English-language adaptation of the Shakespeare play reset in 19th century Havana. The play was translated into Spanish by Nilo Cruz and Alvarez studied the play for almost a year and learned to perform it in both Spanish and English. He later performed in the Actors Theatre of Louisville's 2013 production of The Whipping Man, where he portrayed Caleb, a wounded Jewish Confederate soldier in the American Civil War. The play received positive reviews, and Alvarez received praise for his "nuanced and empathetic" performance. He and friend Gabriel Ebert collaborated on the musical Those Lost Boys, about the one-night-only 10 year reunion of a rockstar band, which was developed and premiered at the 2013 Ars Nova All New Talent Fest and headlined the Ars Nova All New Talent Fest again in 2014.