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.

With her strong angular features and smooth olive skin, Vivien Ong has a special kind of magnetism and hypnotic appeal—the kind that makes you stare and girl-crush hard. But for someone who could easily lean into intimidating model mystique, she does the exact opposite. On set, she is loud in the best possible way, breaking into Singlish, and making the whole studio laugh at her self-deprecating humour. She even fusses over her growing-out hair after having recently shaved it off for Hair for Hope—vanity is clearly not something she clings to tightly. She carries the easy warmth of someone you instantly want in your inner circle. But beneath the chatter sits someone surprisingly introspective.

Winner of The New Paper New Face 2010, Vivien built a career across Paris, Milan, and New York, walking for design titans such as Vivienne Westwood and Anthony Vaccarello. A major early milestone was landing Coach’s global Lunar New Year campaign. “I shot this in New York, very near where I lived,” she says. “It was such a cool experience walking to the set. I basically shot a global campaign at my doorstep.” Behind the glamour, however, was the exhausting reality of the fashion circuit. Vivien moved to New York in 2013 at just 21, fresh off a successful Paris Fashion Week, only to be overwhelmed by the sudden stillness that follows each show season. She describes it as cognitive dissonance: “As a very green model, I didn’t understand that this was the period when not much was going on,” she says. “I just felt like, oh my god, where’s the adrenaline?

“I didn’t have any close friends I could use as a sounding board—I felt like I was just trying to find my own way. It would have been so helpful if someone told me, ‘Hey, just chill. You don’t have to go balls to the wall all the time’.”

To fill the quiet, she turned to unhealthy coping mechanisms. Without a support system, the pace became toxic. “It got to the point where my phone would ding, and I’d start dry heaving,” she recalls. “I’d think, ‘Is it my agent calling to tell me they don’t want me anymore?’ I was living in a very negative headspace.” She took a six-month hiatus to recalibrate—a choice she now calls the best decision she ever made.

There were spectacular highs too, including walking the Etam lingerie show in Paris alongside her idol, Liu Wen. Lined up directly behind the Chinese supermodel, Vivien went straight into fangirl mode. “I was like, ‘Hello, Liu Wen. I’m your fan.’ Then I told her she was the wallpaper on my agent’s phone. Damn malu (embarrassing).”

Her years in the US also exposed her to environments that embraced her extroverted nature. “There were things that I was very insecure about here that felt like less of an issue there. For one, I don’t have a lot of the physical attributes that one considers typical Asian beauty,” she reveals. In Singapore, an agent once told her, “I know you’ve got a personality, but maybe don’t show it.” In the West, her candid personality became her appeal. “They like to chat there,” she says. “After every shoot, everyone goes for drinks. And I’m like, ‘Oh, we can?’”

If there’s one thing she could tell her younger self, it would be this: “So many things in this industry are out of your control, so just show up every day—no need to be perfect, just stay in a good space and keep going.”

A strong advocate for sustainability, Vivien has seen firsthand how retailers prioritise profit over craftsmanship. Yet, while she believes it is important to consume consciously, she is a firm believer in balance and holistic longevity. “Basically it’s not about being perfect but more about the big picture and being able to go the distance,” she explains. “Okay, so you drank from a disposable straw, but it’s out of your reusable mug, cool. You bought a fast fashion piece, but the fabrication is great, and you’ve worn it for years, cool. You lose your s**t occasionally, even though you’re trying to practise mindfulness, also fine.”

Today, at 34, life revolves around her four-month-old daughter. Increasingly, she is less interested in chasing fashion validation than in creating communities where people feel supported. This weekend, she is hosting a panel for new mothers with online retailer Baby Central. “Now, instead of talking about silks and denim, I’m talking about bibs and burp cloths,” she smiles. “But honestly, it’s still the same thing. I still care about quality, comfort, and things that last.”

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