[7] After a difficult and lonely semester at VCU, Toledo transferred to the College of William & Mary, where he would release his next project, Twin Fantasy,[8] a concept album centering around a relationship he was in at the time.

[11] Toledo would release his next full length project the following month, a two-hour-long double album entitled Nervous Young Man, described on its Bandcamp page as "a collection of songs written between ages 17 and 21".

The next month, Car Seat Headrest released the compilation album Teens of Style, consisting of re-recorded material from Toledo's solo discography and was their first record to not be self-released exclusively via Bandcamp.

Shortly after the album's release, Bloom left the group to attend medical school and was replaced by bassist Ethan Ives, who met the band at an open mic.

[27][28] The band tested new material at various live shows in December 2018, debuting the tracks "Weightlifters", "Hollywood", "Stop Lying To Me", and "You Know There's Someone Out There", soon followed by "Can't Cool Me Down" in February and March 2019 performances.

[29][30][31] On June 12, 2019, Car Seat Headrest announced a new live album titled Commit Yourself Completely, featuring official recordings of performances from the Twin Fantasy tour from 2018.

[34] It marks a stylistic divergence from previous material, Toledo describing the album as containing elements of EDM, hip hop, futurism, doo-wop, soul and rock and roll.

[36] The release also coincided with the introduction of Trait, an alternative persona of Toledo's, featured prominently wearing a modified gas mask with blinking LED lights for eyes, and floppy, rabbit-like ears.

[54] Since 2023, Car Seat Headrest have been working on a new studio album that is anticipated to be released in mid 2025, and have slowly begun returning to live performances following Toledo's health issues.

[55][56] AllMusic biographer Mark Deming wrote that Car Seat Headrest created "moody and introspective lo-fi pop tunes that are melodic but structurally ambitious at once".

[57] Writing for Pitchfork, Jeremy Gordon stated that on Teens of Denial, "Will Toledo reaffirms that he is ahead of the pack as an imaginative singer-songwriter, capable of crafting dynamic indie rock.

"[59] Rolling Stone described Making a Door Less Open as "an immersive and adventurous album that sounds polished, but never slick, a well-executed experiment in cross-genre pollination that heightens Toledo’s best songwriting impulses.

"[60] Toledo has been open about his musical influences, which include, but are not limited to, Radiohead, The Beatles, The Beach Boys, Leonard Cohen, David Bowie, The Monkees, R.E.M.,[61] Nirvana, Green Day, The Who,[62] Pavement, Kendrick Lamar,[63] Daniel Johnston,[64] Sufjan Stevens,[65] Destroyer, Frank Ocean[66] and They Might Be Giants.