Sheila went on to attend the Jamaica Commercial Institute, which ultimately led to a secretarial position with Tony Laing at Total Sounds Records. Although the job served to further inspire her musical aspirations, she decided instead to train as a flight attendant with Air Jamaica, due to her grandfather's involvement in aviation with Pan American Airlines. She did not altogether abandon her hopes of making a career in music, however, and through her association with Total Sounds, she concurrently embarked on her musical career with respected producer, Harry Johnson. Her initial recording was a version of the Ebony's 'Life In The Country', although it was her popular version of the Emotions' 'Don't Ask My Neighbour' that led to a series of successful sessions at Harry J's Kingston studio.
In the early '70s, Harry Johnson had issued a hugely successful version of the Dusty Springfield / Baby Washington hit, 'Breakfast In Bed' by Lorna Bennett and with Sheila's voice the perfect vehicle for a reworking of the song, the producer had her re-cut the song in the latest style. This new version even managed to surpass Lorna's interpretation when it entered the British Pop chart in 1979, so inspiring UK-based Popsters UB40 and Chrissie Hind to record it nine years on - their version scoring a Top Ten hit in 1988.
Meanwhile, the success of Sheila's version led to the release of her eight-track album début, 'Sheila Hylton', which featured her most recent works and her next single, 'Disco Reggae Beat'. In 1980, she recorded an adaptation of the Police hit, `The Bed's Too Big Without You' with Jamaica's Riddim Twins, Sly Dunbar & Robbie Shakespeare working alongside Johnson. The recording proved an instant favourite and marked her second foray into the UK Pop charts.
Following her European success, she maintained a low profile until she appeared in the studio recording, 'House On The Rock' for the television documentary 'Deep Roots Music', with her proud mentor looking on. The song was released in the UK on the Carib Blue label with a version of 'Love Don't Live Here Anymore' featured on the flip-side.
In 1984, she released the excellent 'Let's Dance' before leaving for the USA. She has since remained in New York City with occasional visits maintaining her association with colleagues in the Jamaican recording industry. One such trip in 1995 led to her signing with Tommy Cowan's Talent Corporation with whom she enjoyed success with a version of the Supremes' 'My World Is Empty Without You' and the album, 'Stepping', which featured 'We Are In Love' (a duet with the late Dennis Brown), as well as a version of Ken Boothe's 'Freedom Street'.
While in Jamaica she also performed live alongside Boothe and Third World, and hosted the International Reggae and World Music Awards. In 2010, Shelia recorded 'Black Gold And Green (To The World)' for the Jamaican athletics team, proving she was still a winner, and has since maintained her profile with a fine King Jammy's production of 'Angel Of The Morning.'