Winsome began her recording career in 1985, when she signed to South London record company Fashion Records. Her first release on their 'Fine Style' label was a cover of Barbara Acklin's "Am I The Same Girl" recorded at the Mark Angelo recording studios in Clerkenwell London and had Brinsley Forde, Tony Robinson, Angus Gaye and Bigger Morrison (ASWAD) as her session musicians. Deborahe Glasgow, Michael Gordon and Winsome originally provided the BV's for her first track, but the girl's threw Michael out of the session for being too much of a perfectionist! These musicians played on Winsome's first 4 releases for Fashion; "Am I The Same Girl", "Can't Take The Lies", "Born Free" and "Homebreaker".After a meteoric start which had her travelling Europe and England extensively. In 1987 she performed at Reggae Sunsplash on Clapham Common, England to over 300,000 people. She returned to the studio and recorded a number of duets with some male labelmates; "TONIGHT IS THE NIGHT" w/ Gospel Fish, "HOLD ON" w/ General Levy,"BEST YEARS OF MY LIFE" w/ Sweetie Irie, "LET'S START OVER" w/ Frankie Paul, "ROCK WITH ME BABY" w/Nerious Joseph and also with some guest featured artists "SUPERWOMAN" w/ Tippa Irie. In 1989 both Winsome and Tippa were awarded a gold disc for reaching No.1 with their track. Whilst recording with Frankie Paul he told Winsome to "Sing like you're giving birth!" After their labours, a beautiful track was delivered safely.Whilst still under contract to Fashion Winsome featured on many recordings for other labels. She recorded a french version of Louchie Lou and Michie One's "RICH GIRL" with French DJ Big Boss entitled "AH! SI JETAIS RICHE" for French label Bachich. Numerous titles for Anthony Brightly's Sir George label including an album in 1995 entitled "STORY OF A BLACK WOMAN" which included tracks "ONE GIRL TOO LATE" and "YOU'LL NEVER KNOW HOW IT FEELS" to name but two. "YESTERDAY" with Peter Spence for the Stingray label.