In 2019, she founded a country music supergroup called The Highwomen alongside Brandi Carlile, Maren Morris and Natalie Hemby and has also performed as a member of the Texas Playboys, Thrift Store Cowboys, and Jason Isbell & the 400 Unit, as well as in a duo with Rod Picott.

[10] When she was 12, she started taking fiddle lessons in Lubbock from Lanny Fiel, who knew Frankie McCourter from the Texas Playboys.

[11] At the age of 15, she joined the Texas Playboys, the former backing band for Western swing legend Bob Wills.

[13] She has also performed and recorded with Jason Isbell & the 400 Unit, Devotchka, Chris Isaak, Thrift Store Cowboys, Todd Snider, Blackberry Smoke, and Justin Townes Earle.

[14] In 2011, she appeared in the movie Country Strong as one of the musicians backing singer Kelly Canter, played by Gwyneth Paltrow.

In 2018, Shires announced that she was working on a new album, To The Sunset due for release on August 3, 2018[20] which, like My Piece of Land, would be produced by Dave Cobb.

Isbell revealed on Twitter that Gillian Welch and David Rawlings will make a guest appearance.

David Menconi of the magazine Spin said that Shires "sings [...] like an earthbound Emmylou Harris",[15] and her vocals have been likened to those of Dolly Parton.