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News & Insight

A Look Into The Life, Hustle, and Flow Of Street Style Photographers

By Kishore Sawh on October 4th 2015


If you’ve ever thumbed through the pages of virtually any social or fashion magazine in the last half century, what you’ll see are images from professionally orchestrated shoots, and then other images that are probably more compelling, that are almost exactly the opposite. In the past ten years, that second style of image has become a major focus of the fashion world, and where fashion goes, photographers flow. Street style photographers are a breed a bit different than the rest. Living in the limbo between paparazzi and fashion photographer, the street style photographer has become essential to the market.

When you see the images they produce, they tend to bear common traits; a beautiful, if not strange subject isolated from the background via spot metering and likely shot racked out at 200mm or 85mm at 2.8 or 1.4. To the untrained or unappreciative eye, their images may seem simple, technically basic and thus easy to capture. This is far from the truth.


I won’t sit here and argue that the average street style photographer will be able to sit and discuss the finer points of camera mechanics and theory, but since when was a good image only taken by those with that knowledge? What they do is work in a high paced, high energy, fiercely competitive and time sensitive environment and have to pull pretty and compelling imagery out of whatever their surroundings are at any given moment. That’s not easy, and it’s sad when I see photographers look at the images some of these style shooters make, and drop some empirically, factually incorrect utterance about how simple it is, just showing how unsophisticated they are in their thinking.



Let me be clear right now that a good image isn’t simply one that shows off camera skills. That, in fact, is likely a poor image in many cases. That tends to mean you’re making the photo about you, the photographer rather than your subject. It’s akin to Jonathan Ross vs Oprah Winfrey. One talk show host will be chuckled about for a while because they were entertaining, and the other will be remembered because of how much she was able to make it all about the subject, the guests.


Street photographers have to deal with crowds, security, traffic, lighting conditions out of their control, and people who aren’t always paying them any attention, and to somehow pull out compelling images in that environment. The good ones really can make a good living from it, and a meaningful one at that.

I’ve included a selection of videos below to highlight this arena of our world. In the first, you’ll see a video about a day in the life of street style photographer Melanie Galea, which will introduce you to the environment in which her breeds can be found – London Fashion Week shooting for Global Blue. Then, there’s another that actually gives some idea of what street style shooters are looking for, such as the shots they particularly look to get, and the last, probably one of the most impactful and inspiring photographers, Bill Cunningham. You probably know him because he’s a legend, and one who’s been doing this for quite some time – I mean, the who’s who of NYC fashion literally dress in a way they want to be seen by Bill.

Here are the Street Style Photographers I follow most:

FaceHunter (Name I wished I’d have thought of)

Bill Cunningham

Tommy Ton

If you’re interested in this type of look and shooting, check out the film about Bill’s life, and if you want the basic skill set you need to deliver images of this type, then might I suggest Photography 101 as the tool to get you there, like now.

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A photographer and writer based in Miami, he can often be found at dog parks, and airports in London and Toronto. He is also a tremendous fan of flossing and the happiest guy around when the company’s good.

Q&A Discussions

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  1. R B

    The Tommy Ton link certainly doesn’t seem to link to the correct website. I believe it should link to ??

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  2. Ralph Hightower

    Interesting! I watched the video of Bill and I noticed a subtle right thumb movement. Bill shoots film!

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    • Paul Empson

      I’m guessing so did the videographer.. it was footage from way back.. but still packed with good advice..

      I liked and noted that his kit was small, very portable and discrete..

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    • John Cumisky

      Bill was shooting film still until 2 years or so ago when he was finally forced to move over to the digital due to the demands of the NYT photo desk.
      I’m not sure which model as I’m not up on Nikon, but he stuck with the brand and bought one of their consumer bodies, nothing high end.
      He is a fixture of NY and Paris Fashion weeks.

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  3. Paul Empson

    I’ve been in public places and abandoned buildings.. about to be moved on by, security, when they spy the damsel in the dress and suddenly it’s ok.. carry on.. ..maybe they just realise we’re an unlikely couple to cause trouble..

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