Hey there fashion lovers! Today we’re going to dive into what makes a street-style photograph truly iconic. These are the photos that stand the test of time, and continue to inspire fashionistas around the world year after year. So, let’s explore some of the top street-style photographs that will never go out of style!

What is Street Style Photography? 📸👕

Before we dive into the iconic photos, let’s first define what street style photography actually is. At its core, street-style photography is the capture of everyday people in their everyday clothes, on the street. This genre of photography has been around for decades, and often inspires high fashion designers to incorporate trends and styles from everyday people into their collections.

A person taking street style photography of someone in a colorful outfit on the street.

Bill Cunningham’s Biker Shorts 👖👀

One of the most iconic street-style photographs of all time is of Bill Cunningham’s capture of a woman wearing biker shorts in New York City in the late 1980s. This photograph has become an emblem of street style photography, and was even the subject of a documentary in 2010.

What makes this photograph so iconic is the fact that the woman is wearing something so ordinary, yet the way she pairs it with the matching blazer gives it a high-fashion feel. It’s the perfect example of how everyday people can influence high fashion.

A woman wearing biker shorts and a matching blazer, as photographed by Bill Cunningham.

Cindy Crawford’s Red Jacket 🧥💄

In the early 1990s, Cindy Crawford was already a household name in the world of fashion. But it wasn’t until a photograph of her wearing a red jacket was captured by a street-style photographer that the jacket became iconic.

Crawford’s pairing of the jacket with a black turtleneck and matching lipstick became a trendsetting moment in fashion history. Even today, fashionistas seek to recreate this look.

A photograph of Cindy Crawford wearing a red jacket and black turtleneck.

The Sartorialist’s Parisian Chic 👗👠

Scott Schuman, known as The Sartorialist, is one of the most famous street-style photographers in the industry. In 2007, he captured a photograph of a Parisian woman wearing a chic plaid jacket, high-waisted pants, and ankle boots.

This photograph became iconic because it perfectly encapsulates the effortless chic that the French are known for. It’s a testament to the fact that sometimes, the look of a photograph can speak louder than the subject themselves.

A photograph by The Sartorialist of a Parisian woman wearing a plaid jacket and high-waisted pants.

Leandra Medine’s Man Repeller 🕶️👜

Leandra Medine is the face behind the blog Man Repeller, which has since become a go-to source for fashion inspiration. It’s only fitting that one of her street-style photographs became iconic.

In this photograph, Medine is captured wearing a pair of oversized sunglasses that completely hide her face, a floppy hat, and carrying a bucket bag. It’s a bold fashion statement, and helped push the “ugly-chic” trend into the mainstream.

A photograph of Leandra Medine wearing a floppy hat and oversized sunglasses, as captured on the street.

The Power of Iconic Street Style Photography 💪🏼📷

Clearly, street style photography has the power to inspire fashion trends, influence designers, and become iconic in its own right. It’s a genre of photography that is constantly evolving, as fashion trends come and go, but the idea of capturing the everyday on the street never gets old.

So next time you’re out and about, take a look at what people are wearing around you - you never know when you might spot the next iconic street-style moment.

A collage of the iconic street-style photographs discussed in this blog.