Dylan Chong, 38

Founder and owner of Dylan & Son

Dylan Chong Dylan & Son

When we met Dylan Chong two years ago, the tailor – who is distinguished by his minimalist palette and streamlined silhouette – shared his aversion to accessories: “No pocket squares, bracelets, rings – these days I don’t even wear a watch – because I find them uncomfortable when I’m cutting.” Thanks to his recent engagement, however, Chong rediscovered his fondness for timepieces: “Last September, I proposed to my girlfriend, and an engagement watch made more sense to us than a ring.”

I’ve always liked watches, but just did not get around to exploring them. My girlfriend [now fiancee] and I had previously talked about getting an engagement watch rather than the usual engagement ring. A watch made more sense to us since we will eventually get wedding bands, and we don’t want to have two rings.

I’d describe my style as classic – high-waisted trousers with braces, generously cut shirts, gently shaped jackets, dark over-the-calf socks and polished leather shoes. My suits are mostly in solid colours. My shirts are mostly whites and pale blues, with some striped ones thrown into the mix. I still don’t own a pocket square.

When I look at watches, the design takes precedence over everything else. I’m not someone who fusses too much about movements and other technical intricacies. Size is a big consideration for me, and I favour small watches. Chunky sports watches and dress watches with many complications have zero appeal to me.

When I first seriously got into watches, I did quite a bit of research, and sought advice from a couple of friends who are into the game. Two of my favourites are a Patek Philippe Gondolo from the ’70s and a Cartier Santos Galbee from the ’80s. I got them both online – the Patek is from Chrono24, and the Cartier is from a Japanese website run by a watch store in Fukuoka.

The Patek Philippe Gondolo has a mesmerising dial that just appeals to me. The stepped case adds an extra dimension to the watch. It’s the perfect size for my skinny wrist, and I love how slim the case is. I’m always in suits and dress shirts, and this slips perfectly beneath my cuffs.

I wanted a bracelet watch to match more casual outfits. I was looking for a two-tone Cartier Santos Galbee with this chain-link bracelet, and finding one proved tricky. So when I found one in good condition, I jumped. I wear it more on weekends, with jeans and knitwear.

Two timepieces that represent my personal style

Cartier Patek Philippe
Cartier Santos Galbee in steel and yellow gold, and Patek Philippe Gondolo in yellow gold.

(Related: Where to find bespoke suits in Singapore)


Derrick Yeo, 34

Director of a family business

Derrick Yeo

From a denim jacket – sans shirt – and jeans at a Formula One event, to a mesh top and ripped jeans at electronic music festival Ultra, Derrick Yeo has worn some pretty crazy outfits. More soft-spoken in real life than his flashy Instagram account (@trumpster.d; 102,000 followers) suggests, the 34-year-old says: “When I started my Instagram account, I would look at the outfits that other Singaporeans wore in their posts. All the guys wore normal stuff – to me, they were like the good guys. So, I thought, ‘Okay, I’ll be the crazy one.’”

Which came first for me, fashion or watches? Fashion, for sure. When I was 10, I would watch MTV to see what my favourite boy bands were wearing, and try to get similar clothing. But it was difficult, because children’s clothes aren’t as nice as they are now.

Today, what I’m wearing is quite subtle: a white shirt (with a tone-on-tone monogram) and dark trousers by Dior. So, I added these Gucci studded suspenders to make my outfit a bit special.

The watches I’ve chosen to complement my look today are the Urwerk UR-105 CT Streamliner and the Panerai Submersible Marina Militare Carbotech PAM 961. I like larger, sporty watches.

Robert Downey Jr wore a similar Urwerk UR-105 in the movie Avengers: Endgame. His was the Iron version, in titanium and steel, while mine’s matte black. I like the flip top and the self-winding system that looks like jet-engine turbines.

There are only 33 pieces of the Pam 961, and it comes with the chance to train with the Italian special forces, the Comsubin, in Italy. When I ordered the watch, I didn’t know that it came with the experience. But it was fun. I went last September, and got to do shooting and ride in their helicopters, but honestly, I think they just let us do the simple stuff. Not that many of us who went for the experience are that fit. [Laughs.]

I used to be quite unfit, but I started exercising last year. My stomach was getting bigger because I like eating junk food and didn’t work out. I had a Louis Vuitton belt with an “LV” buckle, and I got irritated because the top of the “L” kept poking my stomach. I started working out with a trainer, five days a week.

Anyone can buy designer clothes, but if you want a nice body, you have to work out. You can’t buy it. Otherwise, Bill Gates would be buffer than Arnold Schwarzenegger.

Two timepieces that represent my personal style

Urwerk Panerai
Urwerk UR-105 CT Streamliner in titanium and black PVD- coated steel, and Panerai Submersible Marina Militare Carbotech PAM 961.

(Related: Watch spread: vintage inspired designs)


Arael Boo, 35

Co-founder of a bird’s nest processing and wholesale business

Frequently seen at fashion or watch events decked out in the latest styles from top designer brands, Arael Boo has a distinctively flamboyant style that shapes his wardrobe and his watch collection. And the father of two – who owns a bird’s nest business together with his wife – is not afraid to admit it. Most of his favourite timepieces, including the two that he selected for this feature, are decorated with a healthy amount of bling. Says the entrepreneur, with an even healthier dose of self-confidence: “These watches are rare and dazzling. They represent my style and who I am.”

I’ve been interested in fashion since my teenage years. I was actually interested in watches even earlier. But I had no time for either until recent years, because I fully devoted my time over the past decade to setting up, growing and stabilising my business, as well as my investment portfolios.

In the last three years or so, I’ve built up my “profile” with watch retailers. They were actually very careful and even asked to see my company financials. Now that they are certain that I won’t resell my watches, I’ve been given the opportunity to buy more “unicorn” timepieces that you won’t see on any boutique shelves.

For today’s shoot, I’ve picked my Jaeger-LeCoultre Master Tourbillon Dualtime with diamonds and mother-of-pearl dial, and a Rolex GMT-Master II in rose gold with sapphires, rubies and diamonds. The first is a dress watch and the latter is a sports watch. Both are big, but not too thick, so they fit under shirt cuffs.

I’d describe my personal style as regal, classy and flamboyant. Here, I’m wearing a Dior jacket designed by Kim Jones, Dolce & Gabbana trousers, a brooch by Tiffany & Co, and a diamond Cartier Juste Un Clou bracelet.

For me, aesthetics are more important than technical features when it comes to watches. Complications like chronographs and equation of time are hardly useful in everyday life. My Zenith Defy El Primero 21 Full Diamond has a chronograph that can measure 1/100 of a second and has a double-chain structure, where the time display and chronograph are each driven by independent mechanisms. Did I buy it because it’s a masterpiece of modern engineering? No, I probably got it because it’s framed by five carats of diamonds.

Two timepieces that represent my personal style

Jaeger-LeCoultre Rolex
Jaeger-LeCoultre Master Tourbillon Dualtime in white gold and diamonds, and Rolex GMT- Master II in rose gold and sapphires, rubies and diamonds.

(Related: Fine clothes and accessories bring this stylish tribe together)