Dean will perform at Sandringham Farm in Cape Town on 29 January 2027, before heading to Nasrec Expo Centre in Johannesburg on 31 January. She joins the line-up featuring South African stars Elaine and Zee Nxumalo, alongside Chelsea Sloan and Jade T, with more acts still to be announced.
It’s been a big year for Dean, who won Best New Artist at the 2026 Grammy Awards and four Brit Awards. She’s also had a string of hits, including Man I Need, Nice to Each Other and So Easy (To Fall in Love), from her second album, The Art of Loving.
If you’ve been following the online chatter, you’ll know this announcement has been building for a while. Milk + Cookies kept teasing its upcoming headliner with the question “Who will it be?”, while fans started connecting the dots after noticing that both the festival and Olivia Dean’s Instagram profiles featured the same distinctive pink aesthetic.
@rushe_c @Olivia Dean blink once if it’s you girl. #fyp #tiktoksouthafrica #festival #concert #viral ♬ original sound - RuRu
Naturally, the theories started flying, with Dean’s name among those being thrown into the mix. Now, the speculation can finally come to an end: the Grammy-winning singer is officially heading to South Africa in January 2027.
@enosvlogs if the rumours are true we will be there �������� #oliviadean #milkcookiesfest #southafrica #festival ♬ Rein Me In - Sam Fender & Olivia Dean
Dean’s booking continues Milk + Cookies’ approach of moving between genres rather than sticking to one musical lane. Kaytranada headlined its inaugural South African edition in 2025, followed by rapper Gunna in 2026. Dean brings a different sound to the line-up, with her blend of soul and pop adding another dimension to the festival.
“Never the same sound, always the same feeling,” said Chase Freeman, head of marketing at Milk + Cookies, describing the thinking behind the festival’s artist bookings.
The event also extends beyond its main stages, bringing music together with food, fashion, art and design through workshops, pop-ups, parties and other cultural programming. Local artists, creatives, venues and partners help shape each edition, making the festival a platform for the cities it visits as well as its international headliners.
Since launching in South Africa in 2025, Milk + Cookies has attracted more than 30,000 attendees across Cape Town and Johannesburg, according to organisers.
Pre-registration is open here. Pre-sale tickets are scheduled for Wednesday, 28 October, at 10am SAST, with general sales opening on Friday, 30 October, through Howler.
The festival is open to attendees aged 18 and older. Further artists and programme details are expected in the coming weeks.
