Meet the photographer and videographer who’s going viral for his shots of local fashion moments

For most Singaporeans, chancing upon a video by Orchard Road Fashion would warrant a double take. The first take allows you to appreciate the striking outfit on display, often highlighted in saturated colour and captured in slow motion so you don’t miss a single detail. And then, the realisation hits: isn’t that filmed on Orchard Road?

Another look at the social media handle will confirm your suspicion. Orchard Road Fashion, which you can find on both Instagram and TikTok, is run by Sky, a producer for an ad agency based in Singapore. Citing fashion, photography and videography as his passions, Sky uses Orchard Road Fashion to tap onto his creative side—and showcase Singapore fashion in the process.

Just as New York had Bill Cunningham, and Tokyo had Shoichi Aoki’s Fruits magazine, local street style now get its own spotlight thanks to Sky’s videos, which have racked up thousands of views on social media. He has even turned his lens on Tatler friends at the 2022 Tatler Ball, where he captured our guests walking through the National Gallery in all their dazzling ensembles.

Below, we spoke to Sky to know why he started Orchard Road Fashion and what he thinks makes an outfit worthy of being featured.

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When and why did you start Orchard Road Fashion?

S: I started it around October 2021 (yes, during pandemic). My intention was to promote fashion and see how Singapore can pull off fashion trends.

Why did you pick Orchard Road to be the focus of your street style snaps?

S: Orchard Road, particularly the area in front of the H&M building, is like Shibuya crossing to me. The area has good coverage or line of sight, which is good for capturing different people. Aside from that, it is where the shopping malls are located, as well as luxury brand stores.

What makes an outfit worthy of a post to you?

S: It should showcase a good aesthetic; nice colour combinations; an interesting style, cut or silhouette; and lastly, the person’s confidence and aura. It’s a combination of personal preferences and what my followers want to see gets a person featured. If an outfit sparks joy, then you’re in.

When do you usually hang around Orchard Road spotting interesting looks? How many looks do you capture in a day?

S: I usually go to Orchard Road during the weekends between 2pm and 7pm. At most, I can capture 10 to 25 looks but not all of them can make the cut.

Do you try not to be spotted when you’re filming?

S: Not really. I’m not hiding when taking the videos, I just try to be a bit distant so the camera can capture the full scale. I do want to talk to my subject or followers as that gives me assurance that they feel comfortable and happy with what I’m capturing. But sometimes, capturing candid shots are worth it, because the subjects are more natural. They don’t pretend or act like models walking the street. They are naturally more confident and happy.

How do people usually react when you ask them for a photo?

S: In the early days, many of them did not want to be part of my Instagram or TikTok so I thought of other ways to produce content. Some of the people we feature are happy with it and very few of them have requested to take posts down. Now that Orchard Road Fashion is getting attention, more people want to be featured and roam around where I usually film. Some people even tag me [on social media] to let me know that they are waiting to be featured, or they walk back and forth to be noticed.

How would you describe Singaporeans’ relationship with style, based on what you’ve seen?

S: For me, there are two types of people walking around Orchard Road. Firstly there are those who want a simple, less complicated outfit that they can use from day to day. Then there are those who dare to be different. They want to stand out and show what they like even if weather don’t cooperate.

Do you see a difference in how the various generations dress up?

S: I think there is a difference. The younger generation seems to prefer thrift clothes, neutral tones and minimalist look. The older generation tends to dress up in bright colours and their outfits are not as coordinated.

What do you hope people take away from your Instagram / TikTok?

S: I want to showcase to the world how people in Singapore approach fashion, regardless of their status in life, their gender, look, nationality or religion.

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