Weekends in Orchard Road

I’ve been spending my weekends shooting along Orchard Road in Singapore. This is to force myself to devote three to four hours a week to practice my street photography.

It is an attempt to make it a routine so that I will become disciplined enough to shoot weekly. I haven’t been able to complete a project in shooting daily. So, I’ll start off with a less ambitious attempt and shoot weekly instead.

Street photography - cleaner cleaning the elevator

Looking through my photos, I knew I had to be out there shooting more often. By shooting more, I would increase the chances of getting photos that would be good enough to be included in my portfolio.

I’ve also broken down the project into mini assignments such as capturing shots of street fashion, colour themes, hands, shoes and portraits of strangers. These sub-projects would eventually add up to become a more complete body of work.

Street photography - Looking up at Mandarin Orchard Singapore

 The idea of stopping strangers to take their portraits came from Danny Santos. He’s a street photographer known for shooting 100 strangers in Orchard Road.

Approaching a stranger to ask for permission to take their photo is more daunting than it sounds. Well, at least it is for me. I wanted to step out of my comfort zone and challenge myself.

Street photography - T-shirt Big on winning

I found myself intrigued by the way that people dress. Simple t-shirts with interesting designs caught my eye as well.

Street photography - Man in Orchard Singapore

These photos were shot with my D700 using either the AF-S 50mm f/1.4G or the AF-S 70-200mm f/2.8G VR II. The conspicuous gear caught the attention of my subjects pretty quickly. I had to frame my shot and snap quickly to catch them unaware.

If I wanted to get eye contact, I just delayed pressing the shutter button until they spot me. I had to anticipate the right moment because they would usually only glance over the first time and avoid the camera thereafter.

Street photography - Couple with a child in pram

Street photography - Police motorcycle in Singapore

The warden halted traffic for some VIP’s convoy.

Street photography - Tourist in Orchard Singapore

A lost tourist. He was fumbling through the map for quite a while. That looked like a D90 or D7000 with an 18-105mm. Yes, I have a bad habit of trying to guess what gear others are using by looking at it from far.

Street photography - Red adidas sneakers

These were the shoes that the tourist above wore. I guess it adds on to the lost look.

Street photography - 313@Somerset with Mango advertisements

Street photography - Windows of a building in a repeating pattern

Street photography - A Sikh man on a Vespa in Singapore

I noticed this Sikh gentleman on his classy Vespa just before the light turned green. I had barely a moment to frame and snap before he sped away. His right food had already lifted off the ground when I took the shot.

Street photography - Man with cowboy hat wearing a Mellow t-shirt

Street photography - Man looking up

Street photography - Getting a drink to cool of in Singapore's weather

Street photography - Man riding a bicycle in Orchard Singapore

Street photography - Matching couple looking upwards

Shades, stripes, sling bags, shorts and Crocs. Their syncrhonised feet and tilting their heads upwards just made them look like the splitting image of one another.

Street photography - Man in hat who looks like his t-shirt

He should be standing as straight as the man on this t-shirt to look the part, instead of slouching.

Street photography - Girl riding a bicycle with pink tyres in Orchard Singapore

Hot wheels! I really dig those pink rims. If you don’t already know, pink is my favourite colour.

Street photography - Portrait of a female tourist

After being rejected by one after another stranger to have permission to take their portraits, I was soon becoming disillusioned with the idea. When I first thought of doing it, I had the impression that it would be an awkward task but not one that’s tough. Soon, I realised that most people were unwilling to have their pictures taken by a stranger. It didn’t help that this stranger was carrying a DSLR with a huge telephoto zoom lens.

I was so close to giving up.

I was scanning for my next subject when I spotted this lady. She was obviously a tourist and she was shooting with a DSLR. I figured that photographers would tend to be more willing to have their photos taken. I rattled off my brief explanation on why I wanted to take her portrait. With my heart pounding in my chest, I almost forgot to breathe when I walked over to speak to her.

Before I could dive into my prepared speech, she just smiled and shrugged, “No English.”

She could not understand me. Thinking on my toes, I pointed to my camera and then pointed at her. She gave me a puzzled look. I motioned with my camera to imply that I wanted to shoot her. Understanding dawn upon her as her face lit up with yet another smile. She nodded shyly. I quickly took the shot and thanked her.

I showed her the photo on my camera’s LCD screen. She smiled and gave a thumbs up. She thanked me for the photo and I walked away to leave her to her photography.

I didn’t have my name card ready so I wasn’t able to pass her my contact. I wasn’t able to communicate with her so I was quite apprehensive about getting her contact information. In hindsight, I should have. I really have to thank this lady for being so kind and gentle to a nervous and fearful photographer. She made my first experience with taking portraits of strangers a very pleasant one. And it made me want to take more of such shots.

Street photography - Portrait of an American tourist

It took me a while before I found someone who was willing to be my subject. Once again, it was a photographer.

He’s an American tourist and he was more than glad to let me take a couple of photos after I had explained to him about my project.

He was very patient and allowed me to position him in proper lighting. My first shot had horrible back lighting that was very unflattering. I simply had to shift behind him and place him where light would fall on his face.

After a long day in Orchard Road, I managed to get two shots of strangers. My goal is to reach a hundred portraits.

That might take me a while. 

Learn with me.

Join me in my journey in exploring the transformative potential of AI.


  1. Jen Xi Avatar

    Testing new comment system.

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