How to Shoot Street Style Photography

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I grew up with hip-hop, R&B, and “street culture.” Most of me and my buddies were kids up to no good— constantly roaming the roads, riding our bikes, listening to hip hop, burning and remixing music, rolling around in my 1991 Sentra with 12’’ Subwoofers.

I also grew up quite poor— so I could never afford the cool “streetwear” brands out there. Nike’s were out of the question— Adidas would have to do (funny enough, apparently Adidas is the cool brand).

Anyways, I have always been drawn to street culture and street-wear, and I guess they call it “street style” nowadays (the cool kids probably call it something else, but that definition will have to do for now).

How to approach “fashionable” strangers

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I have always been drawn to interesting characters— and people who dress in a “street style” manner are some of the most fascinating to me. I love the way they are able to mix & match all these different elements (sunglasses, hair, hats, tattoos, chains, shirts, pants, sneakers, etc) while also being comfortable.

If you are the type of person where you are interested in others who are fashionable or rock “street style” — one of the easiest ways to approach someone and say, “Excuse me, I love your look. How would you describe your style?”

Most people (even though they look pretentious) will be quite honored that you identified them and complimented them. By asking an open-ended question like: “How would you describe your style?” really opens up doors.

For example, I just walked around Soho in NYC with Cindy, and there were a ton of kids waiting in front of the “Supreme” store (camping out, waiting for a new season of clothes to drop, kind of how Apple fanboys camp out of the store for the new iPhone). Anyways, I saw some guys who looked really fashionable and I liked their vibe. I first passed them, and on the way back, I approached the “leader” of the group (who was dressed the most flashy of them all).

I approached him and first asked him, “Pardon my ignorance, but what are y’all waiting for?” They kind of first laughed at my ignorance, but because I said “pardon my ignorance” — they were cool with me. I then followed-up by complimenting his style, and asked him to give me some street style 101 education. I asked him, “Why is Supreme so hot, compared with other brands?”

He then got really interested and invested in the conversation, and told me how the guys who design for Supreme— all they probably do is go through thrift stores, and re-purpose styles for the brand. If you have never heard the “Supreme” brand (I knew of it, but don’t know too much about it) they are the hottest streetwear/skate brand at the moment (people will line up for days for their clothes).

I then asked if I could make a few photos of him, and he was very willing. He put on a few poses, and I tried to catch some photos of him off-guard.

Regardless if the photos are any good or not— I loved my conversation and interaction with him. And if there is one thing I learned it is this: the importance of being curious, telling others that you are curious (and ignorant), and asking them to educate you. Don’t feel guilty for “stealing” someone’s time— rather; you are making them feel important, and contributing to their lives.

My love/hate with fashion

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Honestly I think that fashion is a bit of a scam— I do like how it helps people feel more confident in their own skin. I also like how people can express themselves through style. At the same time, I feel bad for all the kids (and adults) who are suckered into thinking that somehow buying a brand (expensive ones) will make them feel more loved by their peers and “society.”

When I grew up as a kid, only the “cool kids” could afford Nike’s and Jordan’s. It was a social marker— and a way of putting yourself in an ivory tower and bragging to your poorer friends.

People who are dressed-up really well might look pretentious and unapproachable, but if you treat them with some curiosity, love, and warmth— they will open up to you.

Above all, try your best not to seem “cool”. The more out-of-touch and ignorant you seem, the more open they will be with you.

Here are some other lines you can use on people who look fashionable on the streets as a way to open a door; and also to (eventually) ask permission to take a photograph of them:

  • “Excuse me, I love your look. How would you describe your style?”
  • “Excuse me, I was walking down the street and your style really popped out to me. Do you mind if I made a few photos of you? I could email them to you afterwards too.”
  • “Excuse me, I just wanted to compliment you on your [article of clothing]. It looks really lovely on you.”
  • “Excuse me, I think your outfit looks great on you. Do you mind if I made a few photos of your outfit?”

I’m sure there are tons of other ways you can open up conversations. But don’t forget, be humble, be curious, and let your subject talk. The more you get your subject to be engaged in the conversation, the more doors it will open, and (hopefully) the more interesting photos you will make.

Also whenever in doubt, ask for permission.

Learn how to shoot street portraits

  1. Free Book: The Street Portrait Manual
  2. How To Get People to Say Yes When Shooting Street Portraits
  3. How to Direct Your Subjects When Shooting Street Portraits
  4. Video Lecture: How to Shoot Street Portraits
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