The oldest of five siblings recalls first falling in love with colour and print while wandering through bales of fabric then sold at the former Metro department store in High Street, during shopping trips with his mother.
By the time he was 17, he was helping her stage a fashion show at the now-defunct Tropicana nightclub in Scotts Road.
"I designed all the clothes, roped in friends to model, choreographed the show and recorded all the music.
"That first show very much set in motion the career I would continue with for the rest of my life," Lee says with a laugh. "I still do the same now - just that now I do it for the National Day Parade."
These days, he tackles myriad projects, which last year included directing the Jubilee year National Day Parade, writing the theme song and contributing to the SG50 finale, The Future Of Us exhibition, at Gardens by the Bay.
This year, ahead of his 60th birthday in August, he will be holding a commemorative concert called Singapop! at The Star Theatre, which will take audiences through his musical life journey, complete with songs and stories to inspire the next generation of young talents.
The singer-composer, who swims at the Singapore Island Country Club and hits the gym at the Grand Hyatt regularly to stay fit, has also found a new hobby: collecting Versace silk shirts from collections that were released before designer Gianni Versace's death in 1997.
The pieces in his collection of fantastically printed shirts have been carefully selected and were bought for about US$1,000 (S$1,340) each from online sites such as eBay. He has more than 50.
"I bought three just yesterday," he says sheepishly. "Nowadays, I visit eBay every day just so I don't miss a bargain."
For him, the shirts are much more than a superficial love of the luxe.
They are also an investment that reflects his deep love for all things nostalgic, given that similar Versace silk shirts were what he wore while performing overseas in countries such as Japan in the 1990s.
"My memories were jogged when I saw an old picture of myself from a concert back in the day," he says.
"But because most of my old shirts were ruined after I ended up sweating through the delicate fabric, I began collecting them again this year.
"I love how bold they are. They've quickly become the pride of my wardrobe."
And that is saying something, given that his wardrobe is every fashion maven's dream - filled with brands such as Tom Ford, Dries Van Noten and Gucci, vintage finds sourced online, bespoke suits by Leslie Chia at Pimabs and all manner of beautiful accessories, including more than 20 pairs of cufflinks that fill a large Godiva chocolate box.
But for Lee, it is evident that style is much more than a fancy brand on a label. His carefully curated home and wardrobe speak of a man who has always been bold, colourful and sentimental, rather than one who is eccentric for eccentricity's sake.
"There is a picture of me performing as a 17-year-old, wearing a shirt that I made myself which has one style of print on the sleeves and a completely different bold print on the body," he says when asked how his style has evolved over the years.
"So I guess you can say I haven't changed much. I've always been this eclectic person. I've stayed true to myself."
And even though he admits with a smile that he now visits doctors for a "little more than getting my temperature checked", he says he has stayed away from any aesthetic surgical procedures.
"I'm open to doing some non- invasive treatments such as Thermage for a little skin tightening once in a while, but that's about it. I've let my hair go grey because I'm not on a mission to look young forever," he says. "To me, youth is much more a state of mind."
One just has to look at the framed mint-condition denim jacket that sits in his study to know that what he says is true.
Covered in colourful patches, it was a purchase he made in Carnaby Street in London on his first visit to the city as a 14-year-old.
Now, he has a grown-up version, a similar Levi's denim jacket covered in a rainbow array of ironed-on patches and badges that he has collected from all over the world. It is a sentimental homage to his younger self.
"Don't get me wrong, I believe very much in ageing gracefully," he says when asked how his style will evolve in the future.
"But what I think won't ever change is that I will always be young at heart. That's something my style will always celebrate, no matter my age."
• This story first appeared in the January 2016 issue of The Life digital magazine.