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Olivia Dean: ‘It’s easy to let other people tell you what you should be doing’

The breakout singer-songwriter has captured the hearts of Gen Z with her honeyed vocals and happy-go-lucky charm. We sit down to talk about her biggest year yet

Olivia Dean behind the bar
Photograph: Jess Hand / Time Out
Photograph: Jess Hand / Time Out
Chiara Wilkinson
Written by
Chiara Wilkinson

To get to know Olivia Dean is to feel like a bit of an arsehole.

It’s not often you come across someone so confident in themselves, so bubbly and yet so self-effacing and generous. Maybe you knew a girl like this at school. She was talented but never conceited. Effortlessly cool, but irresistibly warm. She always looked put together, but didn’t wear much makeup and she was always on time, despite being the busiest person in the room. You end up assuming they’re hiding some sort of monstrous fault. 

The thing about Olivia Dean is that she isn’t.

It’s been one hell of a year for the buzzy London musician. She released her debut album, ‘Messy’ – a breezy pop record loaded with easy grooves and need-to-sing-along lyrics – which peaked at number four in the charts and was nominated for the Mercury Prize. She played her first Glastonbury show, was tipped by Elton John and sold-out venues across the country. When we speak, Olivia is weeks away from setting off on her US tour –‘I’m gonna go do three nights in Brooklyn: it’s bonkers!’ – wrapping up in time to swim with dolphins in Mexico at Christmas.

You’d think that would all be enough to validate any 24-year-old, but there’s still a heavy sense of imposter syndrome lurking in Olivia. As delightful as she is, she hasn’t quite got it all figured out just yet.

Going incognito

Olivia is a London gal through and through. She grew up in Highams Park, a maze of suburbia in the north-east of the city, with her mum, a barrister, her dad, the music lover of the household, and her younger brother. ‘It was like a village,’ Olivia says. ‘One primary school, two pubs and a big Tesco.’ 

She pauses. ‘I didn’t love growing up there,’ she says, a pitch higher. ‘I felt quite different to everybody else. In primary school, I was one of the only Black girls. I think that’s what made me want to get out and go to BRIT [school].’ 

Olivia Dan sitting on a pink chair
Photograph: Jess Hand / Time Out

It’s mid October when we meet at the Ridley Road Market Bar. On the way there, I pass whiffs of wet fish stalls and technicolour fabric troves. Next to the grey sky it all looks impossibly vivid, like the market stalls have had their saturation turned way up, somehow. The bar is an institution many north-east Londoners will be familiar with, but for those less accustomed – or for those too inebriated at the time to remember – it’s an intimately-sized, tropical-themed bar in Dalston, with a revolving disco ball and a black and white chequered floor, usually sticky with spilled slushies and Kylie Minogue prosecco. It’s the sort of place you go on a Friday night when you’re a few drinks deep and want to keep the night going – the sort of place that will have you singing (or shouting) along to ‘I Bet You Look Good on the Dancefloor’ and exchanging numbers with a stranger in no time. 

Today, though, the dance floor is empty and the bar is closed. A team of three shift around Olivia’s chair with laser focus, finessing her hair and makeup. The indie bangers are gone. Instead, we’re listening to a playlist of old school soul, contemporary hip hop – and something that sounds like it could come from the south-east London jazz scene, a part of the city which Olivia now calls home. ‘That’s if I’m ever there!’ she laughs. ‘When you’re away so much, it starts to feel like being on the tour bus and in the airport is your normal state. My flat kind of feels like a hotel.’ 

When you’re away so much, it starts to feel like being on the tour bus is your normal state

She spends her days off cycling to her friends’ houses (she’s on the Lime bikes at the moment because her VanMoof is broken), going to scratch comedy at Matchstick Piehouse and drinking pints at SET Social (she’s a lager lassie, but wishes she was a Guinness girl). ‘It’s nice to walk around and feel like there’s people who look like me, being able to just walk to the Black hair shop,’ she says. ‘South east has a bit of anonymity that I like.’ 

For someone who enjoys her solitude, that anonymity is becoming harder to come by. ‘It is a little strange sometimes, especially when you’re alone and not sure if you’re recognised in a room,’ she says, recalling a time when a girl told her she wouldn’t be able to go to the pub in two years. ‘It can be quite anxiety inducing. I’m really not interested in the idea of celebrity – I want to be successful in music, but my ambition is not to be famous.’

Olivia is an ambassador for Chanel and a regular face at London Fashion Week, so the last part might be hard to buy. But she’s quick to acknowledge the irony. ‘You kind of don’t have a choice,’ she continues. ‘It’s the same with fashion as it is with music. And it’s okay. I’m not – I’m not complaining.’ 

Olivia Dean sitting on a table
Photograph: Jess Hand / Time Out

Throughout our chat, Olivia prefaces any mentions of her wins with a disclaimer, because God forbid she ever came across as ungrateful. She’s careful to recognise that she was ‘very lucky’ that her parents supported her choice to pursue music as a career: ‘I never had the ‘‘that’s not gonna make you any money’’ thing.’ It’s the sort of grating self-awareness that we, Gen Z, pride ourselves on, but there’s a maturity in how she stands by her graft. ‘I’m definitely aware of the privileges to go to BRIT, and I think the title comes with, perhaps, a ‘people-give-you-a-look-in’ assumption,’ she says. ‘But I wouldn’t say that they hand you stuff on a plate. It is a free school in Croydon. You just apply because you know you want to do music and you know you want to work really hard.’

Gut instinct

Olivia jumps up from her makeup chair like she’s been bitten. ‘Sorry, this is not on my playlist,’ she squeals, flapping her hands and running to the other end of the bar while the rest of the room tries to work out the track like it’s the music round of a pub quiz. ‘How embarrassing!’ The opening lyrics from Sleeping Beauty’s ‘Once Upon a Dream’ skip into the next song. 

Olivia studied musical theatre while at BRIT, but realised she wasn’t as dedicated to that world the same way other students were. (She doesn’t rule it out in the future, though: she’d love to be in ‘West Side Story’, or write a musical, one day.) Becoming an artist was her calling. She started her career by collaborating with Rudimental as a supporting vocalist, aged 17, and released her debut EP, ‘OK Love You Bye’, in 2019. There was also a brief stint of studying at Goldsmiths, where she enrolled in a degree in ‘popular music’ before dropping out after three weeks. ‘I wish now that I’d maybe had that uni experience people have,’ Olivia says. ‘I feel like I missed out a bit. Going to uni in London is very different – I wish I’d gone to Bristol or Wales or something. But I was also so set that I knew I wanted to write songs and become an artist, hopefully as a full-time career.’

If I stay in this environment I’ll start to believe that I’m cringe – and I’m not cringe!

Those three weeks at university became part of a wider lesson to always trust her gut: she worried if she studied music too much, it could ruin the playfulness and naivety of songwriting for her. ‘Personally, it felt like you had to be making something really alternative and left to be cool [there],’ she says. ‘I was like, if I stay in this environment I’ll start to believe that I’m cringe. And I’m not cringe!’ And it’s helped to inform her decision making throughout her career. ‘I learned that I know best, which can sound dickheaded, which it shouldn’t do at all,’ she says, on making her debut album, ‘Messy’. ‘It’s very easy to let other people tell you what you should be doing. But actually, at the end of the day, you know immediately what you want to do. I learned that I had to be selfish. And make myself happy first. Who gives a fuck what other people think about it?’

Olivia’s music isn’t trying to be something it’s not: it’s not especially abstract, edgy or intellectual. It’s easy-listening: the type of sweet, milky pop that makes you want to reach for the volume dial in the car, play through your headphones to make the night bus journey feel shorter or send to a friend getting over a breakup. But there’s no auto-tune, no Ibiza-tinged EDM beats which plague a lot of chart music. Instead, there’s a humanness to her work, an innocence in the sound as much as the lyrics which makes it irresistible to her many fans. 

Olivia Dean Time Out cover
Photograph: Jess Hand / Time Out

‘It’s not a straight line when your heart has been smooshed up,’ Olivia says, explaining that ‘Messy’ is about navigating the journey of falling in love again after a breakup. ‘It’s a messy road and I’ve become quite hardened. My heart has got a hard case.’ It’s not all gushy breakup songs or self-affirming anthems, though (although there is a bit of that). Her new single, ‘Ladies Room’, is inspired by a drunk chat she overheard in the toilets on a night out. ‘I was just in the cubicle peeing and I overheard this lady talking,’ she says. ‘She was like, ‘‘Girls, if I could give you any advice, never go out with a man who’s 20 years your senior.’’ I recorded her because I thought it was hilarious. The song originally had her voice at the beginning, but it’s illegal to record people. I was in the toilet queue before, so I don’t know how to find her. Wherever you are out there, you’re my inspiration!’ 

Centre stage 

Wearing a Chanel two-piece as sparkly as her two glinting tooth gems, Olivia is finally in front of the camera. Snap. She makes large, exaggerated poses on the dance floor, her arms angled out ‘like a Zara model’. Snap. Then, she’s crouching on top of a plasticky chequered table cloth in a green Miu Miu knit, curling into a ball like a delicious, oversized olive. ‘This one’s ‘Cosmic Egg’’, she says. ‘We do it at yoga’. Snap. Snap. Snap.

I last saw Olivia at the Mercury Prize awards in September. ‘I found out about the nomination on my best friend’s birthday,’ she says. She’d returned from a day of zen at Hackney Wick community sauna. ‘I was lying in my bed and my manager called me and I just burst into tears. Then I ran upstairs to my friend and I was just crying.’

Immediately, imposter syndrome struck. ‘I was like, oh, they’ve just had to fill a space,’ she says, somewhat earnestly. ‘They just probably whacked me on the side. I’ve just wangled my way in. I think it’s hard for me to see myself as, like, part of it sometimes. Raye, Arctic Monkeys and Young Fathers? You guys are real artists. And I’m just, like, doing it. You know?’

Olivia Dean holding a pink drink
Photograph: Jess Hand / Time Out

That same self doubt crept into her making of the album in the first place. ‘There was a big chunk of time where I was in a pattern of being very self-critical – to the point where you just feel so shit about yourself, comparing your beginning point to everyone else's finished product,’ she says. ‘That is just the thief of joy. I was honestly in quite a depressive state. I got out of it: I’ve been doing therapy and learning how I function and what environment I function best in. Therapy is awesome. It’s a privilege to do – I understand that completely, but it’s awesome.’

She starts playing with a strand of hair between two fingers. ‘When I got to the actual award show, I was like, no, I’m supposed to be here,’ she says. She references a metaphor she’d heard about songwriting: there’s a river of songs that flow through the world, and your job is to just add water and hopefully it can flow as far as it can. ‘Sometimes there’s a bit of an energy like ‘Oh, awards don’t matter’. But it’s about having contributed to British music… it meant so much.’ 

Sugar coated 

As we’re packing up to leave the shoot, Olivia Dean chucks on an ‘Olivia Dean’ embroidered bomber jacket and reaches for a tobacco pouch, rolling a ciggy with perfectly manicured nails (good girls smoke these days). We walk through the drizzle around the corner to The Victoria: I order a soda lime, Olivia orders a cup of tea with a splash of milk and a ‘lil bit of sooks’. Rain starts pounding the window.

We’re there for longer than expected. She smiles, flirts, makes sarcastic jokes and never breaks eye contact. She’s here to please. And, sitting in the corner of a cosy pub, it seems like she’s in her element. Because as much as she loves the glamour that comes along with a career in music, at the end of the day she’s a wholesome soul: in her free time, she burns incense, listens to vinyl and knits scarves for her mum. When lockdown hit in 2020, she packed her band into a happy yellow van and drove around the UK, playing socially distanced gigs to cheer up strangers. After this, she’s going home to watch ‘Bake Off’.  It’s a shell that must crack eventually, right? 

I want people to come and be like, that was the best show I’ve ever seen – that’s the power I’m moving with

‘Honestly, I think I’m just a pretty positive person,’ she says. ‘I’m definitely, like, not bubbly and happy all the time. But I feel like I’m very lucky in my life right now and I have a lot to be grateful for. I pride myself on being a good person, because nobody wants to work with a horrible person. It’s not a productive way to move through the industry.’ 

Olivia doesn’t have a London show on the horizon until next year, when she’ll be playing her big homecoming gig at the Hammersmith Apollo (the show sold out in less than a week). ‘I want people to come and be like, that was the best show I’ve ever seen,’ she says. ‘That’s the power I’m moving with.’ 

Olivia Dean sitting at a table
Photograph: Jess Hand / Time Out

Her eyes are giddy: it seems like after months of growing pains, she’s starting to enjoy it all. Even if she’s still trying to figure things out, as much as any 24-year-old would be, it’s okay that the puzzle isn’t complete just yet. ‘I feel very British, very east London,’ she says. ‘But I’m also not. I have this Caribbean heritage that I don’t fully understand because I’ve never been to Guyana or Jamaica. So, I feel like a mess of things. But instead of being negative, which it was for me when I was younger, I’m trying to make it a positive.’

I stop the recording. As sweetly squeaky-clean as Olivia is, there’s always a cheeky sparkle in her eye which seems to come out when she’s most relaxed. I leave the pub and walk out into the pouring rain, and hear a cackle behind me: ‘Nice to meet you babe! Don’t do me dirty!’

Stream Olivia Dean’s debut album, ‘Messy’, here

Photographer: Jess Hand @jesshandphotography
Design Director: Bryan Mayes @bryanmayesdotcom
Senior Designer: @818FPV
Stylist: Simone Beyene @simonebeyene
Hair Stylist: Pashcan’el Mitchell @pashcanel
Make up artist: Emily Engleman @emilyanglemanmakeup
Location: Ridley Road Market Bar @ridleyroadmbIn

Look one: Olivia is wearing @chanelofficial suit, socks and jewellery and @miumiu shoes.
Look two: Olivia is wearing @miumiu, @prada shoes, @chanelofficial rings and @swarovski earrings.
Look three: Olivia is wearing @amiparis dress and coat, @jimmychoo shoes, @chanelofficial rings and @swarovski earrings

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