Typical street style photography is, at its core, 100% about the subject and her outfit. But not mine. I’m too much of a narcissist not to want to put my own stamp on each picture. My favorites depend less on “a great look,” and more on my own personality; they might depict an unintentionally funny moment, a chaotic scene, or a celebrity breaking from their media training to give good photo.
I dug up pictures with imperfections—bewildered pedestrians, frenzied photographers, dump trucks, mailboxes, and street signs fill the space around these subjects. Maybe they’re not pretty and clean, but I never said I wasn’t a messy maximalist at heart. I even looked for good pics where I’m clearly visible in a window’s reflection in the background, because, hey, I like attention too.
Most best-of lists are compiled by journalists, bloggers, and dudes with a Reddit login, so I’m grateful for the opportunity to pick my own personal faves. Not many people get to write their own legacy! My nostalgic side says my favorite street style year of the Vogue Runway era was the first—2015. But the eternal optimist in me prefers 2025, as each season is of course the best one yet. Anyway, I hope you enjoy this stroll down street style memory lane, and see you again in another 10 years!
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