By Gerald Tan – published 20 May 2026
When I first meet Estelle Fly, she is seated on the floor, a giant pink bow fashioned from cardboard perched gingerly atop her head. Behind the camera’s lens, she appears like a character lifted from the pages of a children’s fairytale book. The overall effect is part whimsical, part dreamscape.
Earrings (worn throughout); jacket; bikini top; shorts; bag, H&M. Stockings, stylist’s own.
Photo: Feedbeng
It is a striking departure from the Estelle most fans and audiences recognise from her. She is, after all, a performer whose presence ranges from the sultry to the empowered. Yet, today’s contrast speaks to her ability to slip between identities with ease.
That instinct for transformation has come to define Estelle’s career. She first tasted fame as part of Sea*A, a Southeast Asian J-pop idol group in the early 2010s. When the group disbanded, it meant stepping into uncertainty. What followed was not a linear ascent but a series of detours (among them, a brief chapter as a flight attendant) before she found her way back to the spotlight. Today, she wears many hats, moving effortlessly between singing, acting, hosting, and content creation.
Top, H&M.
Photo: Feedbeng
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Going Solo
Each transition came with its own lesson. “When I stopped being an idol, I was very young,” she says. “At first, there was freedom, but that quickly turned into a sense of loss. As an idol, so much is decided for you. Suddenly, you don’t know what to do and what steps to take anymore. It was uncomfortable.”
That discomfort, she reflects, revealed a hard truth about working as an independent artist. “You start to appreciate the opportunities you once had. As a solo artist in Singapore, you really have to work for everything. You have to prove yourself before those opportunities come,” she says.
Top; jeans, H&M.
Photo: Feedbeng
If the early years were defined by structure, what followed required something far more innate: initiative. “I used to believe that if you just kept your head down and did good work, it would speak for itself,” she says. “But it doesn’t always work that way. You have to put yourself out there.”
Estelle pauses, then adds, more thoughtfully: “A lot of the best ideas come, for example, when you’re bored, but people don’t act on them. We worry about how we’ll be perceived. Will this look desperate? Will it seem strange? But sometimes, different is exactly what you need, especially if what you’ve been doing isn’t working.”
That willingness to push past hesitation and freely experiment now shapes her work ethos. She also realised that the journey is not hers alone. Rather than working in isolation all the time, she now surrounds herself with a trusted circle she describes as her “sounding board”. “Luckily, the people around me really want to make things happen and not just poke holes. Because of this, I’ve learnt to just express myself first and see how things could work later,” she says.
Related article: Kim Se Jeong On Finding The Perfect Balance And Choosing Joy
Sunglasses; dress; shoes, H&M. Gloves, stylist’s own.
Photo: Feedbeng
Building a Legacy
This newfound freedom of expression underpins her latest EP, Zone. The four-track album, noted for its velvety Korean-inflected R&B layers and late-night pop grooves, centres on heartbreak, escapism, and resilience—matters close to her heart.
“So many amazing things were happening when I was working on the album, but deep inside I felt empty most of the time,” she recalls. At the time, she was navigating through a breakup even as work carried her across the world. She adds: “But those were the moments where I got to sit down to create and write what I wanted to say.” Introspective yet future-forward, it’s little wonder Zone feels like her most fully realised work to date.
Scarf; dress, H&M.
Photo: Feedbeng
For Estelle, the sparks of inspiration often begin in stillness. “I like going to the Asian Civilisations Museum,” she reveals. There, she lets her mind wander while being surrounded by artifacts that are testament to the beauty of craft. “I imagine freely, how something might feel, how a performance could look,” she offers.
Performance, in turn, is another outlet for Estelle to exercise her creativity. Recalling her set at last year’s Waterbomb Festival, her expression shifts at the thrill of being onstage after months of preparation. “I get lost in the moment. I enjoy myself completely. It feels like my spirit lifts when I’m on stage,” she says. “And that’s where confidence comes from. You look your most confident when you’re fully in that space. Being yourself, and being proud of what you do.”
Related article: JISOO On Self-Expression, Evolution, And Finding Her Own Pace
Top; skirt, H&M. Stockings, stylist’s own.
Photo: Feedbeng
Offstage, however, validation arrived in a more personal form. “One of my proudest moments was when my mum told me she was proud of me,” she says. “For the longest time, she worried. She felt she needed to pull me away from this path because I wasn’t earning enough. So for her to say, ‘I trust you’—that meant everything.”
It is a tender moment that reframes the idea of success for Estelle—not as visibility, but as belief. “I used to feel like I needed to be seen, to be chosen, and to be validated,” she says. “But now, it’s less about that. I want to create something that stands the test of time. I don’t think I’ve done that yet. But that’s what I’m working towards.”
Editor-In-Chief: Kenneth Goh
Stylist: Aaron Kok
Photographer: Feedbeng
Hair: Dorene Low/ Tress & Curvy
Makeup: Wee Ming
Photographer’s assistant: Xie Feng Mao
Stylist’s assistant: Ynez Loh
Hairstylist’s assistant: Sito S.T
In collaboration with H&M.
‘ The preceding article may include information circulated by third parties ’
‘ Some details of this article were extracted from the following source www.harpersbazaar.com.sg ’
