British singer Olivia Dean will headline the 2027 edition of Milk + Cookies Festival South Africa, as the music and culture platform expands its footprint in one of the continent’s key live-entertainment markets.

The festival will take place at Sandringham Farm in Cape Town on January 29, 2027, before moving to Nasrec Expo Centre in Johannesburg on January 31.

Dean joins an announced line-up featuring South African singer Elaine, amapiano star Zee Nxumalo, Chelsea Sloan and Jade T, with additional performers and programme details expected in the coming weeks.

Olivia Dean. PHOTO | Milk + Cookies

The announcement positions the festival as a meeting point for international music talent and South Africa’s homegrown creative industry, while extending its appeal beyond conventional genre-based concerts.

From Kaytranada to Olivia Dean

Milk + Cookies launched its South African edition in January 2025 with Canadian producer Kaytranada headlining a debut that attracted 20,000 people. US rapper Gunna headlined the 2026 edition, setting the stage for Dean’s arrival in 2027.

The shift from electronic music and hip-hop to Dean’s soul-inflected pop reflects the festival’s strategy of building its identity around audience experience rather than a single musical genre.

“Never the same sound, always the same feeling,” said Chase Freeman, head of marketing at Milk + Cookies, describing the thinking behind its headline bookings.

According to the organisers, the festival has attracted more than 30,000 attendees across Cape Town and Johannesburg since its South African debut.

Beyond the headline performances, the platform combines music with food, fashion, art and design through workshops, panels, pop-ups and parties. It also works with local artists, creators, venues and partners to shape its programming in each market.

Olivia Dean closed out BBC Radio 1’s Big Weekend in May 2026 with a joyful set which was, as she put it, “magic”. It was Olivia Dean’s first time headlining a major festival. PHOTO | BBC / James Watkins.

The approach reflects a broader opportunity for live-entertainment businesses to develop festivals as cultural destinations, where audiences pay for the overall experience as well as the performers on stage.

Olivia Dean’s global momentum

Dean arrives in South Africa following a major awards run in 2026, including a Grammy win for Best New Artist and four BRIT Awards, according to the festival announcement.

Her second album, The Art of Loving, released on September 26, 2025, has strengthened her international profile. The project includes “Man I Need”, which has also performed strongly on the UK and US charts.

The singer’s rise has been accompanied by a personal narrative rooted in family history. During her Grammy acceptance speech, Dean paid tribute to her grandmother Carmen, who moved from Guyana to London at 18 as part of the Windrush generation.

Olivia Dean at the Grammys. Photograph: Gilbert Flores/Billboard/Getty Images

Her appearance at Milk + Cookies adds an internationally recognised name to a festival whose identity rests on bringing different sounds, audiences and creative communities together.

With Dean headlining its third South African edition, Milk + Cookies is betting that a mix of global star power, local talent and experiences beyond the main stage can keep audiences returning to its summer festival circuit.