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Olivia Dean to headline Milk + Cookies Festival 2027

That's right, folks! The Grammy and multi-BRIT award winner will headline the third edition of Milk + Cookies Festival South Africa.

Marchelle Abrahams
Written by
Marchelle Abrahams
City Expert, Time Out South Africa
British singer-songwriter Oliva Dean is heading to South Africa in approximately two months.
Jack Davison | British singer-songwriter Oliva Dean is heading to South Africa in approximately two months.
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British singer-songwriter Oliva Dean is heading to South Africa in approximately two months. Olivia was announced as the headline act for next year’s Milk + Cookies Festival.

She plays Sandringham Farm in Cape Town on 29 January and Nasrec Expo Centre in Johannesburg on 31 January. Local artists Elaine, Zee Nxumalo, Chelsea Sloan and Jade T were previously announced as the support acts. 

Why Olivia Dean? Why not? The girl has serious vocals and music that calms the savage beast, literally. Olivia keeps popping out bop after bop following the release of her album 'Messy' in 2023. That radio-friendly tune ‘Man I Need’ took over our airwaves and Spotify playlists for a year. And then she returned with a soulful collaboration with Sam Fende on ‘Rein Me In.’ 

Time Out Tip: Milk + Cookies Festival is built in each city it runs in, with local artists on the bill and South African creators, venues and partners shaping the programme.

Olivia headlines a festival that defies genre boundaries. Kaytranada opened the first South African edition in 2025 in front of 20,000 people, and Gunna followed in 2026. A producer, a rapper and a soul singer in three years is the pattern, not the exception.

Olivia headlines a festival that defies genre boundaries. Kaytranada opened the first South African edition in 2025 in front of 20,000 people, and Gunna followed in 2026.
Milk + CookiesOlivia headlines a festival that defies genre boundaries. Kaytranada opened the first South African edition in 2025 in front of 20,000 people, and Gunna followed in 2026.

“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 brings music, food, fashion, art and design together through panels, workshops, pop-ups and parties alongside the festival stages. Additional acts and the full programme will be announced in the coming weeks.

More info:

  • Pre-registration: open now on the website
  • Pre-sale: Wednesday, 28 October, 10am
  • General on sale: Friday, 30 October, via Howler, Cape Town and Johannesburg
  • The event is open to ages 18+ only

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