Mr Wong had then just graduated from Chung Cheng High School, where he was classmates with his future wife, Chee Moh Chin. After he was rejected by the police force, his first choice career option, he settled on a job at West End Tailors.
"At that time, tailors like my uncle were trained by the British, but they didn't know how to impart their skills," he recalls.
"They didn't question why things were done a certain way or why one step had to be done before another. To learn from them, you had to observe and then just hope for the best."
It is perhaps this lack of proper training in his formative years which prompted Mr Wong to give up his business four years ago to head the menswear programme at Lasalle College of the Arts.
Mr Lionel Roudaut, programme director of fashion and textile studies at Lasalle, recalls seeking out Mr Wong after a tailor at Peninsula Plaza recommended him.
"Back then, Thomas was president of the Singapore Master Tailor Association, which is why I thought he had been recommended to me. But when I met him, I realised he was a real goldmine for our students - a true master of the craft and someone with incredible knowledge when it comes to the precision of traditional tailoring techniques. "
In turn, going into teaching led to Mr Wong's decision to relaunch his business. He says: "People often lament that tailoring is a dying trade. But to be honest, I think more young people are looking for that personal bespoke touch which you can't get from an off-the-rack suit. I think that for the younger generation of tailors, the sun is just rising. But there needs to be an opportunity for them to hone their skills and grow."
For the two-term president of the Singapore Master Tailor Association, it is this gap that The Prestigious v2.0 is helping to fill.
The store is managed and run by two of his disciples, one of whom was Mr Wong's Lasalle student. And each piece that leaves the boutique is completely made in-house - a rarity in this age of outsourcing.
With prices for a suit starting at $1,200 and going up to $50,000 for a top coat crafted with wool made with rare and fine Vicuna hair from the South American camelid, it costs a pretty penny to be clad in bespoke. But one glance at the polished shirts and jackets displayed in the tastefully inviting store makes it clear that you are getting your money's worth.
The bales of fabric displayed on the dark wooden shelves are from top English and Italian brands such as Ermenegildo Zegna, Loro Piana and Holland & Sherry.
And there is nary a stitch out of place when it comes to the checkered slim-fit shirts or the suit jackets displayed on mannequins.
The message at the boutique is clear: The suits and shirts at The Prestigious help to make the man.
240 steps, 80 hours to make a suit jacket
Fittingly for a purveyor of style, Mr Wong himself cuts a dashing figure in his electric blue jacket and fitted black pants. The look is completed with a maroon pocket square and striped cherry-red and purple socks.
It is this attention to detail that he wants to drum into his new generation of young charges.
"You cannot become a master tailor without mastering the basics," he says, divulging that it takes 240 steps and more than 80 hours for him to complete a single suit jacket. "It is easy to cut corners but you'll never perfect your craft that way. I don't believe in shortcuts - only perfection."
The middle child of three siblings and the son of an oil field worker and housewife, Mr Wong was born in Singapore, but spent his childhood till the age of nine in Sarawak, where his father worked.
When they returned home in 1956, his father began a transport business. But it ran into financial difficulties and, soon, continuing with school was no longer an option.
Mr Wong, like his older sister and younger brother, had to start contributing to the family at 16. Still, he is optimistic when recalling his foray into the working world.
Describing himself as a curious and hardworking child, he recalls always wanting to feel challenged in his work, even if that meant taking on non-paying jobs to learn something new.
Such as the time he signed on to attend a course by one of Singapore's best cutters, a Mr Lum who had volunteered to teach a class every Sunday at the then Singapore Chinese Tailors Union in Victoria Street.
"Even though I had been working at West End Tailors for three years at that point, going for this free course is what I consider to be the beginning of my foundational years," he says. "Thanks to Mr Lum, I learnt about drafting and chalk lines. It also made me think for myself - about why something was being done and whether it was necessary to include that step in the process."
Not content with knowing how to cut and draft suit jackets and pants, he joined ESE Shirts company in Chulia Street after he left West End Tailors so that he could also learn to make shirts.
Back then, tailors made only jackets and pants, while shirts were made in separate shops.
The desire to learn the art of making the complete suit, including shirts, was so strong, he was willing to start from the bottom again. He honed his skills in shirt-making at ESE for two years until he was poached by a lawyer client who wanted to start his own tailor shop.
From then on, Mr Wong worked in different places - from His Fashions and Arts Tailor in Singapore to a 11/2-year stint at a shop making suits in Hong Kong when he was 25 - learning something new in each job, all the while fine-tuning his own style of custom suit-making.
His wealth of experience culminated in a 19-year-long stay at Fatman Singapore Gents Wear Co. in Jalan Besar, which he joined a month after returning from Hong Kong. It was then one of the most renowned tailor shops in Singapore and the owner, Mr Chew Foo Wah, needed a second tailor to assist him.
As it turned out, Mr Wong was exactly what the store needed. So valuable was he that after six years on the job, Mr Chew gave him the chance to open and run his own outlet, Fatman Pte Ltd, at Grand Pacific Hotel in Victoria Street.
Six years after that, Mr Wong moved to Far East Shopping Centre and, three years after that, moved again to Centrepoint.
Running these outlets meant doing everything from building his own client base to sending telegrams to London to order fabrics. It was also during this time that he began creating his own patterns and methods of drafting - the beginnings of a signature classic style that was grounded in old-school techniques.
But, after 19 years, Mr Wong was itching for a change and decided that it was best to leave. There was also some friction as customers were starting to ask for him by name.
He had entertained the idea of starting his own business, but a pivotal conversation when he first began learning the trade had always held him back.
"Back then, a cousin had told me that tailoring was a very low-paying job and that I should have looked for something that would pay more," Mr Wong says. "I remember then telling myself that one day I would prove my cousin wrong. Not by being my own boss, but instead, by becoming so good at my craft that people would pay me handsomely for my skills."
And they did.
By the 1980s, he was getting an annual pay of $45,000, which, he quips with a laugh, was "enough at the time to get you an Amex Gold Card okay".
But eventually, he knew that the time was right to be his own boss.
The Prestigious was born when a client offered him a space on the third floor of Shaw Centre.
During his 13 years there, he consolidated all the techniques he had learnt over the years and went back to the traditional British way of tailoring clothes, finally arriving at the 240-step process he still uses to craft his jackets today.
The Savile Row techniques came with a high price tag - suits at the time often cost upwards of $8,000 and could go up to $20,000. To attract the right talent, he paid his apprentices four times the market rate with one golden rule - no shortcuts allowed.
Insurance professional Philip Pow, 46, who has been his client since 2003, says: "Mr Wong is an artist first, a teacher second and a businessman third. Going the bespoke route with him is not about being pampered as many think. Instead, it is about the details and small adjustments.
"I have tried other tailors, but I can say that Thomas Wong is still head and shoulders above the competition."
With a strong client base, business went along swimmingly until 2012, when Shaw Centre had to close for long-term renovations.
It was at this point that he was approached by Lasalle to establish and run a menswear speciality course for the school - a decision which went from being a time-filler while waiting for renovations to end to becoming his new passion in life.
After 50 years in the industry, he now sees teaching and mentoring as his purpose. Today, he also sets the curriculum and examinations for the menswear speciality course at Lasalle and provides consultancy services to tailors to help them improve their skills.
For Mr Wong, whose wife is a housewife and son is a professor at Nanyang Technological University, being able to impart his hard- earned skills continues to be one of the most rewarding aspects of his career.
He says of his decision to foster new talent: "I always tell the younger generation to learn a pure tailor's way - no shortcuts. I have always believed in earning from my skill and I want the younger generation to do the same.
"Because maybe one day, someone may steal your designs. But your talent? No one can ever take that away from you."