She returned to the London Borough of Enfield to attend Southgate College, where she studied art.

[citation needed] Her first major acting role was an uncredited part in Gary Oldman's 1997 drama Nil by Mouth, alongside her father.

In 2006, Winstone played the role of Kirsty in the TV mini-series, When Evil Calls.

Winstone is part of electro pop group This Year's Model, brain child of Manchester techno guru DNCN.

She also goes by the stage name "Baby Bo" as part of the London-based hip hop trio Crack Village, a former member being rapper Akira the Don.