Yang Derong is a man with many issues. The kinds that involve local discourse like military service, the Hungry Ghost Festival, viral pentagenarian Chuando, right up to global problems with gravitas like nuclear proliferation and American president Donald Trump.

If that sounds like seriously heavyweight stuff, each topic is addressed in a very social and millennial way: through memes-slash-poster art on his online site Face Of The Day. Yang featured his first post on August 1 and uploads one new image daily (to date, the site already has 39 posts). Each image is rendered in the style of a vintage Singapore calendar and sees him dressing up in full-on character (complete with makeup, wigs, masks, et al) to drill home the message he is tackling.

Just imagine him wearing Singapore flags and streamers as a wig for August 8, because he’s in a “Party Mood”. Or how about a bare-bodied Yang plastered in polka dots stickers and donning a red wig for August 21, because there are just 13 days left for the Yayoi Kusama exhibition at the National Gallery Singapore? But this personal project is not just for laughs. Each post always comes with a link to an article or video about a current topic of the day in the hopes raising awareness about it.

So why does a man, well-known in the creative scene here for over two decades for his work as a fashion designer (besides his own label, he’s worked for Jean-Charles de Castelbajac and was global imaging director for Esprit), set and costume designer (he’s behind costumes for many musicals like Forbidden City), and creative director (he designed the Christmas lights on Orchard Road and art directed the National Day Parade), pull a James Franco? You know, performance art.

“It all started after I decided to take some time out to be a flaneur,” he says of the term that Oxford Dictionaries define as a man who saunters around observing society. He adds: “I wanted to spend more time with my family and give myself the time and a chance to do anything that I’ve always wanted to do but never had the time due to my work and my so-called vagabond life style for the past 30 years.”

In short, it’s Yang’s way of playing the role of a social commentator.

But to mangle a saying, it takes a village to raise an issue. To do so, he pulled together 22 of the top names in the Singapore creative and fashion scene. That roll call includes photographers Geoff Ang, Jet Ho, Micky Wong, Olivier Henry, David Chan; web designer Elaine Tay; digital right-hand man Will Low; playwright and writer Michael Chiang; and hair and makeup gurus Rick Yang, Grego, Ashley Lim, Bobbie Ng, Zennie Casann, Carol Yoong and Nicole Moreira; digital imaging specialist David Tee; costumers Moe, Eddy, Mahmoud; and collaborators Issy Lim, Jacqueline Lim and Yati.

Q: How did Face Of The Day start?

A: I had this crazy thought of collaborating with a group of friends and professionals that I have worked with in Singapore. I thought “Why don’t we get together and do something outside of work that’s non-commercial? Especially with the recent manic and rapid advances in new art, new technology platforms, and social media”. I mean one can do almost anything with a smartphone. So why don’t we start a digital visual dialogue virtually every day for 369 days a year.

Q: What’s the objective of this project?

A: To be a gentle wake up call every day. We hope that it’d be this brief digital visual dialogue that can inspire the viewers to dream, to smile, to think, to question, to laugh, to care, and in times of adversity,  to persevere. Nothing painfully conceptual or very “atas”.

Q: So, can we call you a designer-turned-artist now?

A: Yes, simply because I have been a designer before but I have also been dabbling in other creative media. I guess it’s the norm in the 21^st Century that we multitask and cross different platforms. There are no official boundaries anymore in the creative business and world. The only limit is your own band width. Anyone can do anything now, and it’s never too late. But then again, no, because I’m a flaneur as well.

Q: There is a lot of dark humour with your images. Why is that so?

A: I think that’s a ying-and-yang-type of question. Honestly, they are meant to be witty and supposed to trigger a reaction or emotion in the viewer. So if your perception is “ying”, then there is the “dark humour” side you’re seeing. But if you are looking at the brighter “yang” side, then hopefully it lights up your life. But it has also has a lot to do with the moment when you engage with the visual dialogue, your state of mind and most importantly your emotional barometer at that moment.

Q: What’s with the old-school Singapore calendar?

A: I’ve lived in different parts of the world for 25 years but I have not lived in a place where every race, language, or religion are given equal rights and opportunities. That principle boils down right down to our old-school Singapore calendar where the day of the year is represented in the four official languages, along with the religious holidays of the different ethnic groups.

Q: Ever feel guilty of being politically incorrect?

A: I think I am sufficiently well brought up to not impose any discomfort to someone because of a personal need to express certain thoughts and ideas. Creative expression does not equate to the freedom to abuse. Don’t you agree?

The Questionnaire

My name is… Yang Derong.

Friends and family call me… Derong.

My age is… 52.

The most surprising fact about myself is… I am still alive.

The last thing I did before this interview is… have dinner.

My favourite music to play while working is… silence. I love the openness and emptiness of it.

The proudest moment of my career is… when I have inspired, enabled, and empowered someone with ability, confidence, and happiness to achieve the best in what they want to do.

My biggest inspiration is… life.

My spirit animal is… the unicorn.

If I’m not a fashion designer, I’d be a… teacher.

 My fashion hero is… anyone with great style that’s organically or uniquely his or hers.

The next creative project I’m working on is… a big secret.

Here, we get Yang to share some of his favourite works on Face Of The Day.