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.

To a certain generation of Singaporeans, Lum May Yee remains the ultimate embodiment of ’90s cool. With her luminous skin and cheekbones that could hurt, she helped define a very specific era of Singapore fashion imagery. “In that era, there was a certain look,” she reflects. “You had to be very skinny, very fair. And of course the androgynous look [was a thing at that time] and I think I embodied that when I cut off all my hair and lost some weight.”

That radical haircut would become her signature, leading to major editorial work, a huge Sony campaign shot in Bali, and regional SK-II campaigns across Hong Kong and Taiwan—including the brand’s early Pitera campaigns and one of SK-II’s first sheet mask launches in Taiwan. She blushes when we cheekily mention that some of our male friends still harbour crushes on her. Looking at her glowing complexion today, it is spectacularly easy to understand why they would.

Her entry into fashion—long before modelling became tied to influencer culture or celebrity ambition—was almost entirely accidental. At 18, she tagged along to a The New Paper New Face street casting at Wisma Atria purely to support a friend. “I didn’t really want to do it. But I said, okay, I’ll do it for you,” she recalls. She eventually landed in the Top 10, was photographed by famed fashion photographer Pat Kraal, and slowly began gaining recognition. The true turning point came a year later while she was studying at university, when veteran fashion editor Jeanette Ejlersen spotted her at Zouk. That single night led to her first major shoot with some of Singapore’s most influential fashion names: Photographer Mark Law, stylist Jeremy Tan, and makeup artist Venetia Stravens.

For all the glamour associated with modelling in the ’90s, May Yee remembers the reality being far less polished than people imagined. Much of the work involved marathon catalogue shoots across China and Hong Kong, where models were routinely packed into industrial buildings for up to 18 hours at a time. One particularly traumatic bridal catalogue still lives vividly in her memory. “I had to wear something like 150 wedding gowns,” she groans. “They kept changing my hair, crimping it, pinning it. By the end of 10 hours, I just wanted to go home.” The experience was so exhausting, she immediately told her agency never to book her for bridal shoots again.

Then came her memorable, accidental detour into Singapore cinema. While May Yee modestly downplays her acting chops today—“The film work was really just by the way. I was never a great actress. I think I was a better model”—her roles in Eric Khoo’s 12 Storeys (1997) and the iconic Chicken Rice War (2000) remain enduring, critically acclaimed touchstones of local pop culture. “They are classics,” she says. “You still understand them today because socially, Singapore is still like that—every family has its own issues. That’s life.”

Her most impressive reinvention, however, came when she walked away from full-time modelling at 28 and entered the corporate world. She spent five formative years at Singapore Airlines, rotating across marketing, frontline customer service, and sales. “I had really good mentors. It was a very hard journey after being a model for so many years. But I felt very blessed. People were willing to help me do better in my job.”

Today, at 53, that blend of instinctive style and corporate discipline has evolved into a thriving entrepreneurial chapter. After spending 15 years overseeing marketing and sales for her husband’s family’s fine jewellery business, The Canary Diamond Co., May Yee recently joined design-led lifestyle retailer Antė to lead their marketing and PR team. 

For her, the pivot into retail feels less like a departure from fashion than an extension of how she has always viewed beauty and design. “They might not be super expensive luxury items, but they are exceptionally beautiful and well-made.” Ultimately, from the raw, gritty energy of ‘90s fashion editorials and cult Singaporean films to corporate boardrooms, regional retail strategy, Lum May Yee shows that true style has absolutely nothing to do with standing still. She didn’t just survive the transitions of an ever-evolving industry—she mastered them, proving that the coolest girl in the room is always the one rewriting her own script.

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