The 50 Greatest Street Style Photographs Of All Time

We consume it. We analyze it. We turn to it for inspiration. Street style is transcendent to the point that it's hard to remember a time when it wasn't. Putting together a list on something this subjective is never a simple task, but we made things easier on ourselves. Who better to ensure that this list was as definitive as it ever could be than the photographers, subjects and critics themselves? Four Pins is pleased to present the 50 greatest street style photographs of all time as selected by the Industry's elite.

31 Responses to “The 50 Greatest Street Style Photographs Of All Time”

  1. Mind Game

    To a discerning eye, I’m captured within all those photos. In spirit, style by proxy.

  2. David

    The shot of the girl with the red mesh on her head is amazing. A great takeaway here is that clothes look so much better lived in than in their pristine, unworn state. The people in these photos that understand that inspire me to WEAR my clothes, and to let them do their thing.
    That and the photo of Sean, Nate, Marcus, and Greg captures that warm weather style that can be next to impossible to really master. The posture of that photo is just cool.

  3. L

    I hate to say it, but this is hardly “definitive”. I wish you hadn’t titled this the way you did because while these photos are impressive, they’re definitely not the greatest OF ALL TIME.

    • lawrences

      L, I think based upon the participants this is as definitive of a list as anyone’s ever going to see in one place. What do you think is missing?

      • W

        Certainly as definitive a list as I’ve ever seen though I was surprised no photos of John Wrazej were picked.

      • Seb

        I really appreciate what Four-Pins is trying to do here and I absolutely love all these photos. I think the jury on this was on point and I feel like these are SOME OF the best “street style” photographs “of all time.” But I really have to disagree with the title of this article. 50 greatest “of all time,” is not only audacious and arrogant, Four-Pins seems to be forgetting the roots of origins of street style photography. To say that a group of contemporary photos that were only taken within the past few years are the greatest of all time is just wrong. By saying these are the greatest, you spit in the face of photography and the history here. What about Bill Cunningham? Only one Henri Cartier-Bresson? How many Scott Schumans and Tommy Tons are in here, and yet no Dennis Hopper? I love seeing an Amy Arbus, but you guys should have gone deeper. Yes, these photos are seminal and important to the current canvas of street-style, but you guys are so wrapped up in the now that you are completely forgetting where you came from. I find it mean spirited and arrogant, is all. But I’m mostly just trying to talk about this and not “hate” because these photos truly are some of the best – and you guys are always on point.

        • lololalallll

          “So wrapped up in the ‘now’.”
          I agree completely.
          Most of these photos are of people who look the same like thrift store heros.
          And a girl showing her tits is not style. It’s just shock value because she one couldn’t actually find something “stylish”.

  4. Mike

    Add the wide frame shot from that LIFE Magazines Urban Youths of Watts article and we’re all good.

  5. X2N

    SORRY GUYS THERE IS Photographer AND THERE ARE Snapshot guys SO PLEASE DO NOT CALL A PHOTOGRAPHER ALL THE SNAPSHOT GUYZ …. how can you compare Jamel Shabazz , Cartier Bresson, Dennis Stock… with the new generation who never buy a film and just do one 100 clic on a digital camera to get 1 poor image ???? and last thing where is the KING of street photography > BILL CUNNINGHAM ?????

  6. Andres

    Love it. I think many of these are spot-on, there’s famous one from Sartorialist of guy on nyc street corner rocking red wings, raw denim and blue suit blazer that I’d add. This reminds me of that old adage about how art gives us something to argue about. The most laughable (difficult to defend?) inclusion is LS’s fashion boys playing dress up for each other in SoHo. What criteria was used for that one? “Least likely to inspire anyone to dress like an effete try-hard?”

  7. Andres

    And you got to disclose that you (the author) are (oddly enough) included in the “greatest street photos of all time”. And Nick Wooster exemplifies the critical distinction between fashionable and stylish. He couldn’t be more uncool. And JPeskowitz needs to hold off on the italian pastries if he wants to rock cool patterns or anything kinda out there.

  8. Israel

    Bickering about a list seems like a waste of breath. No matter how definitive it is or how many people are consulted, it’s all a matter of opinion. People will agree on some and disagree on otthis. What’s great about this is sitting back and taking in the showcase of style and flair displayed in these pictures, that’s all that really matters.

  9. Matt

    What a freakin circle jerk. You included a picture of Nico? Seriously guys, maybe leave out the “Greatest” part of the title. This is just a collection of great shots; do it every week. But check yourselves before you start throwing around shit like “greatest of all time.”

  10. Guest

    “Of All Time”. I just can’t get over it. Menswear bloggers and their f’in egos. I hope Bill Cunningham never sees this.

  11. Colin

    Ok so, y’all are going to think I’m stupid, but I need some clarification. Is Street Style just taking photos of randoms on the street who, in the eye of the photographer, have style… or does the photographer have “models” dress up and come out into everyday life and do a kind of street shoot? I honestly don’t know, I’m new to this.

  12. drwe

    48 of 50 makes me physically ill. a photo of people taking photos of people wearing clothes. its like the inception of vapidity.

  13. andre

    “That’s like, your, opinion, man.” – Big L
    (Big Lebowski that is..)


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