Live Review: Olivia Dean’s Evening At The Fleet Steps, Sydney

Olivia Dean’s rise to fame since the release of her debut album, Messy, in 2023 needs to be studied. Since then, she has been shortlisted for the Mercury Prize, scored three BRIT Award nominations, and featured on the soundtrack of the latest Bridget Jones film, Mad About the Boy.

Having never even set foot in Australia until February of this year, her sell-out Evening at the Fleet Steps show in Sydney only nine months later became one of the hottest events of the summer. 

Coming off the back of two incredibly successful supporting stints with Sam Fender in the UK and, more recently, Sabrina Carpenter across North America, Dean’s trip Down Under allowed her to show why she was becoming one of the biggest breakout solo stars of the current era.

Her Wednesday night ARIA Awards performance of Man I Need dominated social media feeds, and, with a heavily rumoured guest appearance at Sam Fender’s Friday night Sydney show, there was no escaping the excitement around her music this week. By the time fans were making their way towards the Royal Botanic Gardens for this show, the anticipation was electric. 

There are few pop-up venues in the world quite like this one: a pontoon stage floating on the harbour, framed by Sydney’s iconic skyline, including both the Opera House and Harbour Bridge. The famous Fleet Steps were swarmed with eager concert-goers who were treated to a quick glimpse of Dean as she was whisked towards the side of the stage in a golf buggy along the water’s edge. It felt like the opening of a festival rather than a single-artist show, a testament to how large her following had grown, and how quickly. With the sun setting and a sea of phones in the air, it was time for the concert to begin. 

Dean arrived onstage in a stunning yellow dress, greeting the crowd with a cheerful, bright-voiced “G’day Sydney!” and offering only one ground rule for the night: have a good time. The crowd did not need to be told twice. She launched straight into early-set favourites Nice to Each Other and OK Love You Bye, both delivered with the warm, conversational ease that had made her so beloved. 

Dean’s relatability, arguably her secret weapon, was on full display throughout the night. At the start of her set, she took the time to greet each pocket of the audience individually, even those who had managed to dock their boat behind the stage.

She then spoke candidly about the stories behind her tracks, turning the concert into something close to a group therapy session with hundreds of participants. Dean did not hide her excitement at playing such an iconic show, telling the audience she had never performed a show like this, which made the moment feel shared, even intimate, despite the scale. 

By the time she played her 2024 single, Time, Dean had settled fully into her rhythm and even found time to gesture a ‘cheers’ to the crowd using a bottle of whatever she happened to be drinking. She continued to introduce hits such as So Easy (To Fall in Love), even finding time to mention that she could see a security guard who she claimed seemed to be “really moving” throughout the songs just behind the huge crowd.

As each song passed, she managed to shift seamlessly between being upbeat and towards a more contemplative tone, a skill which was on show as she moved onto her debut album's title track, Messy, a song centred on the pressures of perfection and the value of allowing oneself to be present, a sentiment Dean herself appeared to embrace. 

Having warmed up the crowd, Dean announced it was time to take it down a notch and that the next few songs would be acoustic. First was UFO, her track about a shy alien searching for somewhere to land, and then followed by Touching Toes, a song performed with only her and two musicians she had played with since she was seventeen.

This section closed with I Could Be a Florist and, by the end of this part of the night, what was most striking was how the once-restless crowd had settled into complete, reverent silence. Dean did not simply perform these songs; she held the audience in place with them. 

She did not leave them there for long, as the emotive stillness that had engulfed the audience dissipated almost instantly when Dean called, “Sydney, are you still with me?” The resultant cheer confirmed that Sydney very much was. She had the entire venue clapping for the next track, Ladies Room, explaining simply that it was about the girls’ toilets. At the end of this energetic, jazz-inflected piece, Dean allowed each of her band members to lean into a solo to close it out. It was a vibrant mid-set surge of energy. 

As the set reached its finale, she refused to play the typical fake-encore game and instead went straight into Man I Need, the immensely popular first single from her latest album. And, almost poetically, just as the last note of her final song of this immense two-hour set, Dive, rang out and Dean walked offstage, the heavens opened. Rain scattered the crowd, but spirits remained high; it felt more cinematic than inconvenient. 

Following the successful ticket sales of this one-off Sydney show back in July, Dean has since announced The Art of Loving tour across Australia and New Zealand for October 2026. Judging by this experience, attending next year’s tour should be at the top of everyone’s 2026 bucket list.