Olivia Dean to Headline Milk + Cookies Festival 2027

Olivia Dean will headline the third edition of Milk + Cookies Festival South Africa in January 2027. The announcement confirms her first appearance at the festival. 

Dean will perform at Sandringham Farm in Cape Town on January 29, 2027, then head to Nasrec Expo Centre in Johannesburg on January 31. She will be joined by Elaine, Zee Nxumalo, Chelsea Sloan and Jade T. Organisers have confirmed that additional performers and details of the festival will follow in the coming weeks.

There have been rumours among fans about who will headline the festival. Promotional material featuring a pink colour scheme prompted some social media users to connect the campaign to Dean.

Photo: Instagram/@OliviaDeano

Dean arrives in the country following a successful period in her career. Her second studio album, The Art of Loving, was released in September 2025 and topped the UK Albums Chart. The project includes, single Man I Need which topped the UK singles chart in October 2025. 

Dean won the Grammy Award for Best New Artist in 2026 and collected four BRIT Awards. During her Grammy acceptance speech, she praised her grandmother Carmen, who moved from Guyana to London at the age of 18. 

“I’m a product of bravery,” Dean said . 

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Milk + Cookies Festival first edition took place in 2025, with Canadian electronic music producer Kaytranada as the headline act. American rapper Gunna headlined the 2026 edition. 

The festival’s first edition reportedly attracted approximately 20,000 people, while its audience has continued to grow across the two cities.

Photo: Instagram/@Poppulsesa

Chase Freeman, head of marketing at Milk + Cookies, explained the thinking behind the festival’s varied bookings.

“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.”

If you are planning to attend, pre-registration opened on October 23. The ticket pre-sale is scheduled for Wednesday, October 28, at 10am, followed by general sales on Friday, October 30, through Howler. The festival is open to people aged 18 and above.