By Lehlohonolo Lehana.
Photo Credit: Lulu McArdie.
English singer-songwriter, Grammy and multi-BRIT Award-winning artist Olivia Dean will headline the third edition of Milk + Cookies Festival South Africa.
Dean will perform at Sandringham Farm in Cape Town on January 29, 2027, before taking to the stage at Nasrec Expo Centre in Johannesburg on January 31.
Sandringham Farm is a new home for the Cape Town leg. The 2026 edition was at Kenilworth Racecourse, and the 2025 debut was at Ostrich Farm.
She joins the previously announced line-up of Elaine, Zee Nxumalo, Chelsea Sloan and Jade T.
The announcement comes after fans speculated about the festival’s headliner, with organisers confirming Dean as the latest international star to join the event.
“People keep asking how Kaytranada, Gunna and Olivia Dean end up on the same bill,” said Chase Freeman, Head of Marketing at Milk + Cookies. “Never the same sound, always the same feeling. That’s the only brief we’ve ever had. We book for the people in the room, not for a genre, and they come for what the room feels like as much as the name on the poster. Three years in, that’s what South Africa has given us.”
“We came here to put on a show and ended up building something with the people who live here, and it’s changed how we do this everywhere else.”
The festival is part of the wider Milk + Cookies Music Week programming, which organisers said would be confirmed in the coming weeks.
The 27-year-old London-born singer-songwriter, whose mother is Jamaican-Guyanese, came up through gospel church singing and busking around London, and she studied at the BRIT School. Her soulful, warm pop sound earned her a Mercury Prize nomination for her 2023 debut Messy.
Her second album, The Art of Loving, arrived in September 2025 and changed everything. Man I Need went to number one in the UK and Australia and peaked at number two on the Billboard Hot 100. Dean also became the first female solo artist to have four songs in the UK Top 10 at the same time.