One of the first musicians Astley recorded with was Richard Jobson. Together with John McGeoch and Josephine Wells, they created a musical backdrop for Jobson's poetry. This work was released as The Ballad of Etiquette in late 1981. Later, Astley went with Jobson to perform in Japan. She also worked on other people's projects, including work for Les Disques Du Crépuscule label, playing piano and arranging music for Richard Jobson and Anna Domino. She also had a track on From Brussels with Love in 1982. Sessions followed with Richard Jobson and Russell Webb for the final Skids album Joy, which featured Astley on flute and as a backing singer. Astley recorded a solo album, She Stood Up And Cried for Crépuscule but this was withdrawn, eventually being released three years later as Promise Nothing. She signed with Why-Fi in mid-1981 and recorded an EP called A Bao A Qu, the title taken from a Malayan legend featured in Jorge Luis Borges's 1967 Book of Imaginary Beings. This was produced by Jon Astley and Phil Chapman. Using a demo studio in Wapping called Elephant Studios, Astley recorded the song that was to place her in the indie top 10 (#8) in 1983: "Love's a Lonely Place to Be", a song of despair and anxiety in spite of its Christmas carol sound. The song would later form part of the 1986 LP Hope in a Darkened Heart. In 1982 Virginia also played piano on her brother-in-law Pete Townshend's album All the Best Cowboys Have Chinese Eyes.
The album From Gardens Where We Feel Secure was released in August 1983 and was recorded on Astley's own label Happy Valley and distributed by Rough Trade, which has since reissued it. The album achieved a place in the top 5 of the indie chart (#4), but neither single nor album was listed in the mainstream charts.
In 1983 Virginia established a more permanent lineup with string players Audrey Riley, Jocelyn Pook and Anne Stephenson, with guests such as drummer Brian Neville and composer Jeremy Peyton Jones.
In 1984, Astley played keyboards on tour with Prefab Sprout around the time of their first album, and she also did sessions for their Kitchenware Records labelmates Martin Stephenson and the Daintees.
In 1984 Virginia signed to Arista but left to join Elektra Records UK. "Darkness Has Reached its End" and "Tender" were both recorded at this time. When Elektra UK folded she went to WEA where she subsequently recorded the album Hope in A Darkened Heart with Ryuichi Sakamoto producing in 1986. The success of this album in Japan meant that Virginia was asked to sign to Nippon Columbia with whom she recorded a further two albums, All Shall Be Well in 1992 and Had I The Heavens in 1996. The following year, the first track from the album, "Some Small Hope" was released, a collaboration with David Sylvian.
Since then, Astley has guested on CDs by both Hideaki Matsuoka and the Silent Poets. Rough Trade re-issued From Gardens Where We Feel Secure with a new cover in 2003, and in 2006 she released her first album of new material in ten years. Entitled The Words Between Our Words. This mini album features Astley reciting her own poetry to a backing of harp music. In 2007, she premiered a long poem "Ecliptic", with flute, harp and birds