Man Behind ‘Orchard Road Fashion’ Takes Videos Every Weekend, Wants To Stay Productive When He’s Not Working

33-Year-Old Man Is ‘On Duty’ Every Weekend For Orchard Road Fashion

Behind the many confident faces caught traipsing along Orchard Road is a man armed with his camera, standing patiently in wait.

He spends hours training his hawk-like gaze on troops of pedestrians outside the H&M building on Grange Road.

A commanding aura catches his attention. He lifts his camera to capture them in action, sauntering down as if the world was their runway.

And that’s how the magic of Orchard Road Fashion begins.

We meet Sky, the 33-year-old videographer behind the viral social media account that has taken young Singaporeans by storm. He tells us of his journey on our Little Red Dot and how it led him on the path of being a personal paparazzi for every fashionable Orchard-goer in his free time.

Spending hours capturing footage for Orchard Road Fashion

It was a cloudy Sunday when we went down to Orchard to meet Sky. Barely an hour past lunchtime, and he was ready to spring into action with his DSLR.

“I’m usually here on Saturdays and Sundays from 2pm to 7pm. I don’t take toilet breaks, nor do I eat,” he told us nonchalantly. We were shook, of course. His sheer dedication was admirable.

Sky explained that he didn’t want to miss a single person who had the potential to be featured on the Orchard Road Fashion account, even if it was just a 10-minute break, and even if it rained.

“If it rains, I’ll wait it out and still look around for interesting people.”

To the uninitiated, Orchard Road Fashion is a TikTok and Instagram account that shines the spotlight on fashionable everyday folks who walk the streets of Orchard.

Sky captures and edits all videos, and it is a one-man team effort.

About 15 to 20 seconds is all it takes to cross the busy junction between the H&M building and Mandarin Gallery. But it’s more than enough time for this experienced videographer to immortalise his next feature for the social media account.

By the time he gets home, he would have around 40 to 50 drafts to review, edit, and publish, much to the satisfaction of his followers.

Looking out for fashionable, confident individuals

What does it take for one to be featured? Sky said it was more than wearing colourful, stylish outfits.

Part of it is how the person walks and how confident they look. They must look happy with what they wear and exude an aura.

He likened it to the spark we feel whenever we see someone on the street who makes us turn to get a better, longer look. “That’s the prime criterion.”

Although Orchard Road Fashion was incepted in October 2021, it only took off around mid-2022 as more people shared his videos — and the same desire to be seen on the platform.

Hence, Sky stressed that inclusivity is key. No matter your religion, race, sexual orientation or body shape, you’ll get the chance to be featured if it’s the right fit for you.

“The only limitation is that I won’t feature kids, teens, or those wearing super revealing clothes. I have to be more mindful about the content — what’s right and not right for the page,” he noted.

Working on Orchard Road Fashion keeps him ‘sane’

Publishing content for Orchard Road Fashion takes a lot of work. But believe it or not, it is only a side hustle for Sky to pass the time productively during the weekend.

Sky works full-time at a local ad agency. Due to the nature of his job, honing his creativity was his top priority.

“As a creative, I need to sharpen my mind all the time, especially if I have no projects going on for the time being.

“Doing local content also helps me with my work because I get a better understanding of the local market,” he said, adding that he moved from the Philippines to the Lion City a few years ago to pursue a career in advertising.

Asked if he had enough time to rest before getting back to the 9-6 grind on weekdays, he said it was enough.

In fact, having the persistence to work on Orchard Road Fashion, in his words, keeps him sane.

Not everybody he shoots will make the cut

Given how big the page is now, Sky said some followers anticipate his presence during his usual hours, so they can bring on their best look and try their luck at getting featured. Disclaimer: there’s no guarantee that they would.

Some also come up to him to strike up a conversation as they want to know more about the person running the page.

“I’m more than happy to connect with them. But I always tell them that the page is not about me — it’s about the featured individuals.

“Without them, the page wouldn’t generate this much buzz,” he shared humbly.

Even though he’d love to feature every person he captures, sadly, he said not everybody has a 100% chance.

Every weekend, he is able to shoot 20 to 25 individuals, with at least 70% of them making the cut. “Sometimes, they don’t, simply because my focus or framing was off.”

Admitting it can be stressful at times, Sky said the pressure is more intense after he obtains the person’s consent and their social media handles for tagging.

“It sounds like I’m promising them the feature, so it can be rough when the quality of the footage doesn’t meet publishing standards,” he sighed.

Even so, he does his best each time and vows not to disappoint future features.

Dealing with hate comments & online trolls

The rise to fame often comes at a price — dealing with negativity. And despite his best efforts, Sky is not spared from this.

Rather, he’s been anticipating it since it’s part and parcel of the social media experience. Initially, he’d try not to respond to hate comments. But silence could only do so much.

He realised he had to intervene and actively moderate them.

Sky would also take the extra step of asking the featured individual if they wanted the comments section turned off. “I’ll let them decide whether or not they’re okay with it.”

Nowadays, he’d pay extra attention to potentially controversial features and look out for trolls who would flood the comments section.

“I’ve also turned on the review function to gatekeep every comment before they’re published. Those that are plain insensitive and offensive will be removed,” he stressed.

It’s my mantra not to be too emotional when reading something. Put your intellect first, and then you can approach difficult topics more reasonably.

Singaporeans seemingly prefer simple, functional outfits

After months of observing Singaporeans in the heart of Orchard, where even the sloppiest of us would make it a point to dress a little nicer, Sky deduced that we city folk prefer simple, comfortable clothing. Also, walking on the safe side is easier than experimenting.

“I think they (Singaporeans) don’t have the time to buy something new or don’t have the time to explore as much. That’s why most people like to wear something functional on weekdays. Then on weekends, it’ll mainly be stuff from Uniqlo or H&M.

“They wear what they can afford because they put money into different things,” he said.

To promote the idea of dressing well in Singapore society, Sky suggested that clothing stores can consider hiring a style expert who offers fashion advice to customers on the spot.

“If they’re on their own, they’re probably not open to buying something without knowing it’ll look good on them. This expert can be the dedicated person to seek advice from and to give customers the confidence they need to rock something different from their usual style.”

Making a difference on his off days

To those of us who cherish spending our off days resting at home before the new work week begins, it’s commendable to see someone like Sky, who prefers staying productive to improve his creativity.

His little TikTok account has also grown to almost hitting 40,000 followers at press time, creating a ripple effect among aspiring fashionistas.

Singaporeans love being in the spotlight more than they’d like to admit. People are going to stare in one way or another, so it’s best to make it worthwhile when they do.

Watch Sky’s favourite featured individual so far:

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