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Street Style Lessons From Bill Cunningham’s ‘On the Street’ Series

Posted on 14 April 2015

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The original purveyor of street style, The New York Times’ Bill Cunningham, has decades of photos under his belt. He pioneered the concept before it had a name and before fashion blogs existed. The octogenarian is still capturing style on the streets, and he brings the pulse of fashion to the newspaper’s readers every week, telling stories and spotting trends.

One can’t help but be inspired by his work, as the passion for what he notices and knows is palpable. In recent years, he’s been narrating a brief background story to go along with the written word and visual slideshow of his pictures, which adds tremendous value to the images. Some of my recent favorites include “Spring Unfurls” and “The Gales of March,” which set a nice stage for different approaches to talking about personal style. Here’s a few observations that I’ve made from Cunningham’s street style photography and editorial work that could come in handy when thinking about your approach to personal style blogging.

Be Natural with Your Style

Some of the most sophisticated, coolest looking people he photographs are those who seem to have gone with their gut instinct when it comes to style. They aren’t overly dolled up, highly orchestrated, or impractical, but just have an innate way of composing a look, pairing things together, being themselves. Most of them are on the way to work or on a lunch break, and this is just how they dress on an average day.

Surely he photographs people here and there that appear to be in a costume of sorts, but the majority of the looks tend to be pragmatic, and relatively easy to wear. With personal style on a blog, I see some bloggers who tend to overdo it, giving in to an unattainable fantasy look, which certainly may have its audience, but is not something that we can all relate to. It seems that with Cunningham, those who don’t expect to have their photo taken on the street are those he gravitates toward. Effortless chic, not procured chic, is the natural choice.

What is the Story that You’re Telling?

In the few examples I shared above, Cunningham fluctuates between the state of the weather and a mini lesson in New York City history, working within other themes of culture, society, and geographic location. He creates an inviting, not isolating, experience told through the clothes and the people he spots, so that no matter where we live, what we’ve experienced, or what our style is, we get the context and significance of what he’s sharing. He’s a benevolent storyteller, and incorporates a unique point of view, alongside humor to reveal what trends are radiating from the sidewalks of New York City.

He could just say “here’s the trend I see on the street this week,” without much of a back story, but isn’t it just so much more compelling with the way he does it? In our own personal style blogs, I’m sure readers would love for you to pen about some of these items, for example the history of the romper, or how a particular piece came to be part of your wardrobe, or why you chose the place you did for the photoshoot, etc. There’s always a unique story to be told!

What do You LOVE About Sharing Personal Style?

I spoke of being relatable, expressing functionality and practicality in your wardrobe, and telling a story, but you’ve also got to remember that only you know your blog’s content and readers best, so carve these concepts into the shape that may work best for you. Cunningham also covers the balls, galas, fashion week, and big social events for the paper, as well as public cultural happenings, like the Easter Parade.  He does enjoy witnessing the fantasy aspect of clothing, but you can tell that overall, he most enjoys observing (and photographing) people who truly exude happiness in what they are wearing.

Clothing is so transformative, and so personal; what about sharing personal style do you most treasure? There must be something, right? Otherwise, you wouldn’t spend all that time in front of the camera sharing your looks. Tap into what aspect of it gives you a thrill, and talk about it on your blog, on your Instagram account— wherever you share your pics, your passion, and your inspiration.

If you’d like to learn more about Cunningham and his work, check out the documentary from 2010, “Bill Cunningham New York” .

[Photo via IMDB]

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