"[4] Winstone first attracted attention when in the late 1960s she appeared at Ronnie Scott's Jazz Club sharing the bill with Roland Kirk.

[4] Interviewed in 2020, she said: "I went along to a gig at the Charlie Chester Club and I sat in with a drummer called John Stevens and he was incredibly enthusiastic and jumped up and said, 'I'm going to tell Ronnie Scott about you, he should give you an audition!'

I think I was on cloud nine...." This led to her first radio BBC broadcast, which by chance was heard by singer Carmen McRae on a visit from the US, who met Winstone and was interviewed for a jazz magazine with her.

"[7] Winstone contributed vocals to Ian Carr's Nucleus on that band's 1973 release Labyrinth, a jazz-rock concept album based on the Greek myth about the Minotaur.

... A must for fans looking for something as cozy as a golden age chanteuse, but without all the gymnastic scatting and carbon copy ways of many a contemporary jazz singer.

[14] Well respected as a lyricist, she has also written words to tunes by Ralph Towner, Egberto Gismonti, Ivan Lins, Steve Swallow, and other musicians.

[22] In 2019, Enodoc Records released the CD In Concert, a remastered recording of an August 1988 performance by Winstone and her ex-husband John Taylor at London's Guildhall School of Music and Drama, including music by Leonard Bernstein, Steve Swallow, Egberto Gismonti, Ralph Towner and Dave Brubeck, among others, with lyrics by Winstone herself, Johnny Mercer and Margaret Busby.

[23][24] Awarding four stars to this collaboration between Winstone and Taylor, Roger Farbey of All About Jazz wrote: "What In Concert demonstrates above all else is the extraordinarily synergistic relationship that this virtuosic pair shared.

[28][29] With Azimuth With Neil Ardley With Joe Harriott and Amancio D'Silva With Nucleus With Paul Rutherford and Iskra 1912 With Eberhard Weber With Kenny Wheeler