What happens when you gather five Singapore models from entirely different eras into one studio for a full-day shoot? Apparently, a lot of screaming, laughter, oversharing, and enough backstage stories to fill a second issue.

At one point, Lum May Yee reminisces about being shoved into a suspicious van and being driven to a dodgy industrial building in China for an 18-hour-long shoot. She was handed a thick envelope of hard cash after. Across the room, Vivien Ong recalls an off-beat shoot in a love hotel where she’s wearing bondage attire and clinging for dear life to a pole over a heart-shaped bed. You can already imagine the gaggles of giggles that ensue.

There’s a reason why we brought together five extraordinary women from different eras of Singapore fashion for our June issue. Gen X pioneer May Yee, with her then-signature pixie cut and androgynous beauty, helped define an era. Vivien, free-spirited and proudly vocal, provided a “how to” on surviving—and succeeding—in the Big Apple. Kaci Beh, armed with an iPhone, represents a new generation of models balancing runway life with social media presence while Sheila Sim emerged in an era when models successfully crossed over into entrepreneurship and mainstream celebrity.

Then, there’s Diya Prabhakar, who arrived at a time when fashion was finally beginning to confront its longstanding diversity problem. Together, these industry heavyweights chart a fascinating evolution of Singapore fashion in the past 30 years—dressed in Chanel’s Métiers d’art collection, no less.

To sit and listen to these women share their stories is to learn that a trajectory in fashion never runs in a straight line; there are bound to be bumps along the road. But, as the saying goes, what doesn’t kill you makes you a superwoman.

As the conversation shifts from castings and shoots to loneliness, ageing, and the quiet exhaustion of constantly being watched, May Yee reflects matter-of-factly, “Modelling was one chapter of our lives. Now everybody has moved on to different things. That’s just life.”

Ultimately, what connects these women most strongly is not the clothes, campaigns, or magazine covers, but their ability to consciously evolve. Together, they mirror the shifting landscapes in fashion that women have had to navigate over the past three decades—from rigid beauty ideals and body image struggles to visibility and social media burnout in the digital age. Read on as they reflect on the highs, the hard truths, and the lives they built beyond the runway.

Long before she was a staple on local television or a practising mental health professional, Sheila Sim was widely regarded as the undisputed blueprint for the modern Singaporean supermodel. Discovered at age 16—by former model Celia Teh at the wedding of her aunt, Ivy Chng (herself a premier ‘80s runway icon)—Sheila’s rise to becoming the definitive face of the 2000s was meteoric. Striking a masterclass pose alongside our cover stars, she exudes the kind of effortless authority that only comes from being one of the most experienced women in the room.

Throughout that golden decade, she cut her teeth across major global fashion capitals, walking trunk shows all over the world. She was the global campaign face for designer Ashley Isham, fronted heritage campaigns for Poh Heng Jewellery, and made history as Singapore’s very first brand ambassador for skincare giant SK-II, joining the ranks of Cate Blanchett and Tang Wei.

Yet, sitting in the studio today at 42, Sheila doesn’t sugarcoat the brutal realities of that era. “I mean, we all have humble beginnings, right?” she laughs. “Modelling to me is a skill set—a character-building exercise on how to deal with rejection after rejection!”

She vividly recalls a traumatic casting in Milan (circa 2003), waiting in the freezing cold for two hours, only for a casting director to glance at two pages of her portfolio, slam it shut, and dismiss her without a word. “The opportunities given to Asians then were much fewer. They were so racist. I had a really miserable time in Milan,” she shares, adding that she also grew up with body dysmorphia issues. “The skinnier, the better. The sample clothes are made so small, and if I couldn’t fit into it, I blamed myself. Now, I think: ‘Design bigger lah! Why must I fit into your clothes?’ But back then, I thought it was my fault.”

The runway also brought its share of PTSD, particularly under the strict, high-pressure direction of legendary fashion choreographer Rizal Ahyar, who enjoyed terrorising his favourite models. “Seven in the morning, on the microphone, he’ll be screaming: ‘Sheila Sim! Call yourself a top model? Can’t even walk properly!’”

She recalls an unforgettable show in Indonesia, wearing a long gown and 19cm wedge heels on a steep, zigzagging stage. On day one, she tripped and sprained her ankle. On day two, another model accidentally kicked her heel and broke the strap, which made her lose her balance and fall off the runway. “Stumble, stumble, stumble, like the memes you see on the runway, and down I went,” she laughs. “There was this mini lamppost right beside the stairs going down. I held on to it for dear life, only to realise that it was not real, and it gave way!” Fortunately, a nearby security guard caught her before she headed backstage to collapse into tears. She promptly called her manager to filter out shows that involved long dresses and sky-scraping heels.

Her ultimate pivot from runway icon to actor, and now into mindfulness coach, wasn’t a corporate strategy, but an organic pursuit of deeper meaning. Today, she is completely re-anchored by an ongoing journey into positive psychology, life coaching, and her current studies in psychotherapy and counselling.

The deeper empathy these have fostered has seamlessly bled into her acting. She recently wrapped production on BYM, a moving local film produced by Gateway Entertainment. Loosely based on true life, she plays a caregiver opposite veteran Hong Kong actress Rossane Lui, who portrays her eccentric, ’80s getai-singer auntie with dementia. “It really helped me to appreciate the world of a dementia patient—it’s very fragmented,” she says. Under the guidance of an acting coach, the experience was completely eye-opening and enriching.

“I realised that I love learning, as you can see with my courses—it has been such an invigorating few years.” She credits her unshakeable, no-nonsense groundedness to her family values, and watching her aunt Ivy navigate the modelling industry with poise and professionalism. “I grew up with a very clean image of what modelling is like,” she says. “We stay humble, we are not showy, and don’t spend money on the wrong stuff.” Today, she is highly intentional when she shops and appreciates thrifting in Japan.

Sheila’s evolution from modelling icon to actor, mother, and mental health coach isn’t a series of erratic career switches, but a deliberate compounding of wisdom. Each chapter has given her deeper insight into the human condition, allowing her to step in front of the camera today entirely grounded, self-mastered, and thriving in her own skin.

Makeup Artist CLARENCE LEE using Chanel Beauty
Hairstylist RICK YANG
Photographer’s Assistant EDDIE TEO
Stylist’s Assistant NAZIRA LUBIS