Grammy and multi-BRIT Award-winning singer Olivia Dean is heading to South Africa as the headline act for the third edition of the Milk + Cookies Festival.
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.
She joins the previously announced line-up featuring 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.
A festival that refuses to stick to one genre
Dean’s booking continues Milk + Cookies Festival’s approach of bringing artists from different musical backgrounds to South African audiences.
The festival made its local debut in 2025 with electronic music producer Kaytranada, who performed for an audience of 20,000 people. American rapper Gunna headlined the 2026 edition.
With Dean, known for her soulful sound, taking over the headline slot in 2027, the festival is once again moving in a different musical direction.
According to Chase Freeman, head of marketing at Milk + Cookies, the intention has never been to build a line-up around one genre.
“People keep asking how Kaytranada, Gunna and Olivia Dean end up on the same bill,” Freeman said.
“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.”
Freeman said the festival’s South African editions had also influenced how the brand approaches events in other markets.
“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,” he said.
More than just music
Beyond the headline performances, Milk + Cookies Festival incorporates food, fashion, art and design into its programme, with panels, workshops, pop-ups and parties planned alongside the main festival stages.
The organisers say local artists, South African creatives, venues and partners play a role in shaping the experience in each city.
Further performers and details of the wider programme are expected to be announced in the coming weeks.
With Dean joining the bill, the festival is continuing its experiment with a line-up that brings together different sounds and audiences for its third South African edition.