Desmond Tan is no stranger to covers; they’ve punctuated every chapter of his life. From his early days in the industry, where youthful energy and ambition defined him, to the more seasoned actor we've come to know, each interview has captured the essence of the different stages of his life.

But this one feels different. There’s a sense that he’s stepped into a new phase, one that’s about inner transformation as it is about outward success. He has a daughter now, and with that comes a shift—a deepening, a quiet assurance and a fresh perspective on life that wasn’t there before.

Perhaps it's the 17 years spent in the industry, but the insecurities that once clung to him like shadows in his youth have softened, giving way to self-acceptance. External measures no longer dictate his perception of himself, and he doesn’t seek validation from them either. It takes a certain level of nuanced understanding of oneself and the world to get there, but it makes perfect sense given his favourite film is Wong Kar Wai’s melancholic In The Mood For Love.

This digital cover feels like more than just a feature but a reflection of a man who has embraced his past, matured into his present and is ready to step into the future with newfound clarity. It’s a snapshot in time, one that perhaps, years from now, his daughter will look at and see not just her father, but a man who once grappled with self-doubt, anxiety, and identity, and emerged stronger for it.

ESQUIRE SINGAPORE: You're a father of a newborn. What was your initial reaction when you first held your baby?

DESMOND TAN: At first, I didn’t feel much when I saw her in the labour room—there was so much adrenaline. But once everything settled down, emotions hit me all at once. It was magical. I held her for the first time about six or seven hours after she was born, after all the checks were done. The moment felt surreal; like time stood still. It was just like in the movies, where the camera zooms in from a wide shot of the earth, then to the continent, then to Singapore, and finally into that very room. It was a heartwarming and moving experience, and even now, talking about it gives me goosebumps.

ESQ: How has fatherhood been treating you so far?

DT: I’m loving every moment of it. I haven’t felt frustrated or regretful. Everything’s been smooth, and I feel blessed to have an easy baby. Fatherhood has given me a new perspective on life, made me grow, and changed my priorities for the better. I now focus more on the quality and intrinsic value of things. It’s motivated me to push harder in both life and work, and I believe it’s expanded my emotional range as an actor.

ESQ: What are you currently working on?

DT: I’m working on a production called Devil Behind the Gate, where I play twin brothers. It’s one of the most challenging projects I’ve ever taken on because I have to portray two very different characters with opposite personalities.

Switching from one brother to the other on the same day is challenging, with all the necessary makeup, wardrobe, and character changes. But I enjoy the challenge, even the tough parts because I believe growth comes through deconstruction. This project is helping me build a new foundation for bigger opportunities.

ESQ: You've a daughter; how's it going?

DT: She’s an easy baby—sleeps from 8pm to 8am. But that means I often don’t see her awake. I leave early for work and by the time I get home, she’s asleep. The only time I see her awake is through photos or a baby monitor during my lunch break.

It reminds me of having a Tamagotchi—those virtual pets we had growing up. I turn on my phone, watch her through the camera, and sometimes talk to her through the speaker. At first, she would cry when she heard my voice, but now she recognises it and doesn’t cry anymore. It’s funny when I think about it.

ESQ: What's something you've always dreamt of doing with your child, even before having her?

DT: When I was younger, I imagined having a son to play soccer with, go biking, or camping. But when I had my daughter, everything changed. There are so many things I want to do with her—read books, sing duets, teach her music. The one song I always sing to her is “A Whole New World” and I hope that, one day, we’ll sing it together. It feels like a special bond between us, like the song is our theme.

ESQ: You entered MediaCorp when you were 21. How has the industry changed since then?

DT: The industry has evolved a lot, especially with the rise of streaming platforms. When I first started, people mainly watched TV for entertainment, but now there’s so much competition from productions around the world. We have to adapt to the changing tastes of both local and international audiences.

The way people consume entertainment has changed too—formats have shortened, and social media has become a big part of the industry. I used to see myself strictly as an actor, but now I realize I need to wear multiple hats. Social media helps promote our work, and I’ve come to embrace that.

ESQ: Are you interested in exploring other mediums like international film?

DT: Always. International interactions have opened up new opportunities, and I’m eager to take on international projects. Working on sets with different cultures and experiences always brings out something new in me. It’s exciting, and I’m constantly inspired to grow and explore more. I don’t want to be a wallflower in this industry—I want to leave a legacy, to be a beacon of inspiration for my generation and the next.

ESQ: What is your favourite film of all time?

DT: Definitely In the Mood for Love by Wong Kar Wai. The film captures the beauty of that era in Hong Kong—the costumes, like the iconic cheongsam worn by Maggie Cheung, the silhouette of Tony Leung’s suits, the hair, makeup and music.

I’m particularly drawn to the performances in the film. Tony Leung and Maggie Cheung’s portrayals, the subtlety, and even the silence in the movie speak volumes. The film’s understated emotions hit me more than the loud action of blockbuster movies. For example, the back shot of Maggie Cheung sobbing in the shower is powerful without showing her face. It’s these kinds of cinematic choices that show the power of film.

ESQ: Are you an introvert?

DT: I think I’m a mix, like everyone. We’re all somewhere on that spectrum. Over the years, I’ve become more extroverted, but I still have introverted moments. I get exhausted after being around a lot of people, but I also enjoy sharing things I’m passionate about. I’d say I’m about 80 per cent extroverted, though I’ve never taken the Myers-Briggs test.

ESQ: As a self-proclaimed "Ah Beng," do you ever feel a sense of imposter syndrome at fancy events like fashion week?

DT: I used to think of myself as an "Ah Beng," but I’ve realised I’m more of a heartlander, a local Singapore boy. I often felt out of place at high-society events but over time, I’ve grown comfortable in my own skin. I’ve learned that everyone has doubts, and it’s okay not to know everything. What matters is accepting your weaknesses and being willing to learn and grow, even if it’s just a little each day.

Now, I’m confident in who I am and my background. I don’t see it as imposter syndrome anymore; it’s just part of my journey. I enjoy meeting people at events without feeling the need to prove myself—it's about embracing who you are and owning your story.

ESQ: Do you struggle with small talk?

DT: When I was younger, I did. I felt the need to prove myself, to be recognized, and taken seriously. But as I matured, I realised that doing less is more. When you’re comfortable with yourself, people can sense it, and they’re drawn to you. It’s important to just relax, enjoy life, and share your passions. Over time, I’ve learned that the key is to be comfortable and positive. When you’re relaxed and enjoying yourself, others will want to be around you.

ESQ: When I was doing research for this interview, I came across an interview you had where you talked about how anxiety is one of your biggest fears. Is that true?

DT: My anxiety stemmed from my struggles with language as a child. In this industry, you’re expected to be strong in expressing yourself, which was difficult for me. The pressure of recorded interviews and live shows added to my stress. As a perfectionist, I put extra pressure on myself, which only made things worse.

ESQ: How did you overcome that?

DT: But over the years, I’ve learned to accept who I am—both my strengths and weaknesses. Accepting yourself makes you feel more comfortable and less anxious. You can’t treat anxiety with anxiety, but you can treat it with self-love and love for others.

Being a father has also helped. I’ve read books on parenting that focus on psychology, and I’ve learned that our anxieties as adults often stem from childhood experiences. By revisiting those events, you can unlock and overcome your fears and anxieties.

Photography: Hong Seong Jip
Art Direction: Joan Tai
Styling: Izwan Abdullah
Grooming: Haruka Tazaki
Producer: Oh Seoyul
Photography Assistant: Woo Do Kyun

The Onitsuka Tiger Autumn/Winter 2024 collection is available exclusively at the Onitsuka Tiger Flagship Store at B1 -37 Takashimaya Shopping Centre and online.

When TOMORROW X TOGETHER made their way to Paris for the closing of the Fashion Week Men's Autumn/Winter 2024 show season in January this year, they were given the complete Dior experience. The quintet did the usual touristy things—visiting the Louvre and strolling around the Seine—but also had the opportunity to visit La Galerie Dior, the exhibition space located within the House's iconic 30 Avenue Montaigne address.

Throughout their adventures around Paris, TOMORROW X TOGETHER were dressed completely in Dior Men, ranging from artistic director Kim Jones' more casual streetwear-leaning proposals to impeccable tailoring that stayed true to the haute couture spirit of the House. The latter was on elegant display as the group entered (to a cacophony of screams and camera clicks, no less) the show space of the Dior Men Winter 2024 runway show at Paris' École Militaire in the city's seventh arrondissement.

TOMORROW X TOGETHER's outfits were a calculated move, both by the group as well as the House. Tapping on his own personal experiences and roots—as he often does time and time again at Dior Men—Jones' inspiration for the Dior Men Winter 2024 collection revolved around the perceived reality of a ballet dancer's life versus the actual reality of it. The ballet dancer in question is Soviet-born Rudolf Nureyev, one of the most renowned male ballet dancers in the world and just so happens to be a friend of Jones' uncle, photographer and former ballet dancer Colin Jones.

Before delving deeper into the inspiration behind the Dior Men Winter 2024 collection, it's important to note that the very beginnings of the collection was an exploration of Monsieur Dior's own relationship with ballet. English ballerina Margot Fonteyn is said to have first discovered the house of Dior in 1948 while on a trip to Paris and became a fan of its creations. A friendship with Monsieur Dior naturally developed and Fonteyn often chose to wear Dior on numerous occasions.

This is where an almost unbelievable happenstance begins. Fonteyn's most famous dance partner is none other than Nureyev—effectively linking Monsieur Dior and Jones in the most amazing way.

"When Colin became a photographer, he maintained strong links to the ballet world and, in 1966, Time Life asked him to document a day in the life of Nureyev, regarded by some as the greatest male ballet dancer of his generation. Bonded through their shared history and mutual sense of fun and mischief, the pair went on to forge a great friendship," explains Jones.

The resulting Dior Men Winter 2024 is one of contrasts: the difference between ready-to-wear and couture, between onstage and backstage, and between the life of Nureyev theatrically and in reality. "Here, it is a meeting of the dancer's style with that of the Dior archive," expresses Jones.

There's no doubt that Jones is already more than familiar with crafting from points of contrasts. His oeuvre at Dior Men has always been merging elegant signatures from the archives with contemporary stylings. The Winter 2024 collection takes references from Saint Laurent's time at Dior, translating the late designer's tailored volumes, vents, pleats and necklines. The iconic Bar jacket created by Monsieur Dior is contextualised once again, this time, combined with Jones' very own Oblique tailoring.

While the runway collection is imbued with more extravagant flounces as well as the debut of Dior Men's haute couture—as nods to Nureyev's theatrical career—the dramatic flair as seen on TOMORROW X TOGETHER are more nuanced. '60s- and '70s-inspired tailoring are cut with a rigid straightforwardness, especially in the single-breasted variations, that are then paired with gently flared trousers. Conversely, the collection's more commercial pieces lend a more streetwear air. Take this as the contemporary equivalent of a dancer's off-duty look with slouchy cardigans and hoodies worn over essential white T-shirts and paired with the roomiest of trousers.

It may be a stretch to compare the duality of Nureyev's life with that of TOMORROW X TOGETHER's, given that the former didn't have to contend with the accessibility of social media and in turn, the almost instant, global fame achieved by TOMORROW X TOGETHER. Yet, what remains a similarity is in the versatility and adaptability of both to weave in and out of their lives onstage and off that echo that contrast of two opposing worlds within the Dior Men Winter 2024 collection.

Photography: Brett Lloyd
Animation: Joan Tai

ESQUIRE: When I think about your collaboration with Tiffany & Co., the first thing that comes to mind is the heart-shaped sunglasses that Alexandre Arnault posted on Instagram. You revealed those sunglasses last June saying, “You would know that I’m engaged to Tiffany. This is just the start of the many things we’ll be doing together.”

PHARRELL WILLIAMS: Those sunglasses are special. Generally, jewellery and accessories are must-have items in my style. That’s why I really enjoyed the process of working on that project. Thanks to the love those sunglasses got, we were more excited to release Tiffany’s new Titan collection. I’m close friends with Alexandre Arnault. So, getting the opportunity to create the Titan collection with Tiffany was an honour, and I’m thankful for it. 

ESQ: What did you want to express with the designs at Tiffany, and was there anyone or any incident that inspired that?

PW: I’m very inspired by water. The design of this collection and the name “Titan” were inspired by Poseidon, who is the king of Atlantis (a fictional city under the sea) and the ruler of the sea. “Atlantis” is also the name of an area in Virginia Beach where I grew up. Also, titanium was named after “Titan”, and you can call it “titan” for short. It is also a name that emphasises our use of black titanium, which we used in this collection to physically embody the beauty of the colour black. 

ESQ: I think it was a great idea to pair yellow gold with black titanium, and it felt fresh to me. 

PW: [The reason for that was] because it is different from tradition, and something unheard of. We wanted to make something beautiful yet different at the same time with this collection.

ESQ: You’ve even mentioned that “jewellery is the punctuation mark of a person”.

PW: Jewellery makes a person. We even remember a person by their jewellery. I can never forget the ring that Slick Rick wore a long time ago. I remember trying to look for the same ring he wore. 

ESQ: There was a dinner party hosted in New York to mark the launch of Tiffany’s Titan collection. Please tell us more details about that party.

PW: I was really happy that my friends and family came and supported me. That was the first time I saw other people wearing pieces from this collection. I was able to give life to this collection while working very closely with Tiffany’s in-house design team, and it’s such an honour to lead Tiffany into a new generation. It was at the New York flagship store (which looks down into Central Park). Launching the collection there made it feel like everyone came back and got together in their hometown.

ESQ: There was a Tiffany Wonder party in Tokyo recently. 

PW: Firstly, I love Tokyo. It’s one of the cities I love, and the food is amazing. It was great to be able to celebrate 187 years of Tiffany in Tokyo.

ESQ: How would you describe the style of this collection in one word? And tell us why.

PW: People. That’s because everything I create is for the people. It doesn’t matter what your gender, race, ethnic group, or anything else are. I hope people of different classes can wear this collection.

ESQ: I recently checked out your collection “Son of a Pharaoh” which you put up for auction on the auction site JOOPITER, which was launched a few years ago. Everything was great, but the BBC Varsity Jacket was especially interesting. It was an item that expressed a politically correct message in a very cool way.

PW: I really love that jacket. Women are our future. I think it’s important to use one’s art or platform to spread love and talk about injustices. Ultimately, it’s because we are all people. I’ll also be launching a very interesting auction on JOOPITER this coming autumn during Frieze Seoul. I don’t want to say much about it now, but I’ll be revealing more details soon, so look out for it. 

ESQ: You’ve been active for over 30 years. How have you been able to stay on the front lines of trends for such a long time?

PW: That’s an interesting point. It’s because I’ve never put in much effort into trying to stay afloat of the trends. I just do what I think is right. I’m also lucky to have worked with interesting people from designers to artists, musicians, and all sorts of other geniuses. I’m learning from them every day.

ESQ: I’m curious as to how you would differentiate something good from something bad.

PW: We can never know what is good, or what people can relate to. You just have to feel that it’s right. Whenever I’m creating something original, or whenever I’m pushing myself to do something that nobody else has done before, that’s when I create "something good". Nobody might like what I created, but we have to be prepared for that!

ESQ: Have you ever thought about how you make that distinction? For example, when I asked you earlier “What is good?”, you could either prioritise your personal preference when doing music or fashion, or you could consider the preference of the consumer. 

PW: I try to look through the consumer’s point of view as much as I can, because I’m also a consumer. I think about how I can make it practical, or how the final piece can improve my life or help me live a better life. That’s the criteria I use when making decisions. 

ESQ: What do you ultimately consider to be “good”?

PW: “Good” is such an interesting word. Why do we not say “great”? But at the same time, there isn’t a singular definition of “good”. Something might be “good” but might not change your life. Or “good” could be just a feeling. But if you don’t have true passion or sincerity, or if you’re trying hard to get “something good” without knowing why you’re doing it, then that attempt will fail. What sets you apart from others is what makes you special.

ESQ: What does creativity mean to a creative director?

PW: I have three roles. The first is to be a student, the second is to share the code, and most importantly, the third is to help others. Every season, we have to start from the beginning and expand the codes, which are the elegant tailoring, comfort, resortwear vibe, the basics, and of course the dandy. At the head of it, my role is to give energy (to the people I’m working with). But if I’m not able to create something charming, none of these have any meaning. I speak through my vision and through the amazing talents at our Maison.

ESQ: In a previous interview with Vogue, you described a creative director as a “love movement” and someone who “commands 2,500 soldiers”. I know that The Love Movement is also your favourite album by A Tribe Called Quest, but to be honest, I don’t understand that figure of speech.

PW: “Love Movement” or “LVers” for short was inspired by the slogan of my hometown Virginia, which goes “Virginia is for Lovers”. The work that our team at the Maison and I do is one part of the strong “LVers” community that we created, and at the same time it’s for the community. The reason I likened it to commanding solders, is because I lead 55 departments and 2,500 skilled artisans at our Maison. It means that my role in this place is to lead and direct. Our work has to be in harmony, and my role is to make sure everyone moves as one. And the basis of all our work is love.

ESQ: How did the slogan “Virginia is for Lovers” come about?

PW: I think it started from an ad or a billboard inviting people to come to Virginia for their honeymoon. But the slogan is true. There are all types of love in Virginia. It’s full of communities and families everywhere. 

ESQ: Hearing that reminds me of the Princess Anne High School Varsity Jacket that you put up for auction. It’s clear that it’s an important piece that explains your identity.

PW: Princess Anne High School is the name of the high school I went to in Virginia Beach! I really love that place, and it’s a place that has a lot of good memories. Coming from Virginia is very important to me and to who I am now. Whenever I have the chance to show that Virginia holds a special place in my heart either by representing or mentioning the place, I’ll take it. Creating the Princess Anne High School jacket was a tribute to my hometown.

ESQ: For someone who has only lived in Korea, it’s hard to picture Virginia as clearly as I can picture New York or LA. What kind of place is it?

PW: It’s a really cool place, and it’s my pride. People might underrate us, but you cannot find the history or the culture we have in Virginia state anywhere else! I love being close to the water and get a lot of inspiration from water. Being close to the water helps me feel safe. 

ESQ: You really love Virginia. What about making Pharrell’s Virginia, just like Donald Glover’s Atlanta series?

PW: That’s an interesting thought. But I’m not sure if Virginians would want a show created about them. If you want to watch a cool programme about Virginia or want to hear about the lives of people in Virginia, there is a documentary series called Voices of Fire about Virginia’s choir group with the same name. It’s amazing how much talent they have. The choir is led by my uncle Bishop Ezekiel Williams, who is an inspiration to many people, and you can catch it on Netflix. 

ESQ: As someone who loves honky-tonk, the Louis Vuitton Autumn/Winter 2024 show was very impressive. I’m curious about the reason why you interpreted Western American outfits in the collection. 

PW: I wanted to reference my personal journey from my hometown of Virginia to Paris. I also wanted to tell the story of Western America, which is also the origin of workwear. Workwear evolved from denim which the first cowboys wore. I wanted to tell the story about this inherent history and express the origin and evolution. The story is told as is in the code of this collection. I’m very proud of that collection. From the buckles to the engravings, we didn’t miss a single detail. Simply put, we elevated every element you can think of up a notch.

ESQ: Will you consider interpreting American kung fu culture from the '70s and '80s in future works? I think it would suit you well.

PW: Kung fu and martial arts in general are very interesting. It’s a sport that requires a lot of strength, agility and patience. It’s almost like dancing. This sport is a type of art. It’s something I could consider!

ESQ: What do you think is your greatest asset right now?

PW: I will forever be a student. I love learning from others, and I get inspired by others every day.

ESQ: It’s interesting that you said “student”. What kind of student are you?

PW: I’m a student who observes well and asks a lot of questions. I want to know what happened here and there. I’m curious about how something I’m seeing is being made and why it’s made. We need to keep having curiosity. It’s the best way to learn about ourselves and the world around us.

ESQ: Is there a personal treasure that you’ll never put up for auction no matter what?

PW: There are so many! You mentioned the Tiffany heart-shaped sunglasses at the beginning of this interview. I will never put that up for auction, because it marked the beginning of my beautiful relationship with Tiffany.

Photography: Hyea W. Kang
Fashion Editor: Yun Wonghee
Styling: Matthew Henson
Grooming: Johnny “Cake” Castellanos at H.Q.E
Tailor: Alice Chastel Mazin
Production: Bae Woori
Art Designer: Kim Daesup
Styling Assistant: Marine Gabaut
Translation: Astrid Ja’afarino
Animation: Joan Tai