The Evolution of Celebrity Street Style in Photos

A street style image is just what it sounds like: a photograph taken of a person outside, often in an urban setting, showing off their outfit. It's been an important form of visual storytelling—whether it's a photo for the most glamorous fashion magazine or documentation of a person walking down the street. Street style photography arose as a genre in the 1920s and '30s, thanks to lighter handheld cameras, and it became popular in the '50s and '60s. We can track its evolution most clearly with celebrities; they're more likely to be captured, both for a photoshoot or by the paparazzi, in a "natural" setting. Over the past several decades, street style has grown in ever-more impressive ways. Below, the evolution of celebrity street style in photos.

Jean Shrimpton

Did you know that "fashion" street style photography wasn't popularized until model Jean Shrimpton started working with photographer David Bailey? He later said that he photographed women the way he saw them, and it made his models (Shimpton especially) more accessible.

Twiggy

"Natural" street style fashion photography began achieving prominence in the '60s. Thus, that decade's top supermodel—Twiggy—can be found posing on the stark streets of London (King's Road, to be exact) in the mod miniskirt that she became known for.

Brigitte Bardot

Part of Brigitte Bardot's innate appeal was her "messy," everyday style—here, she walks barefoot on the streets of Capri, Italy, in between shooting Jean-Luc Godard's movie Le Mepris. Because of her popularity, her likeness was often captured in the street by photographers and paparazzi.

Jane Birkin

There are few people more representative of the Swinging Sixties and Bohemian Seventies than Jane Birkin. To this day, her street style photos (sometimes with partner Serge Gainsbourg) are still some of the most well-known instances of casual, but intensely chic, style—including her classic white tee and basket bag.

Diane Von Furstenberg

Designer, entrepreneur, and future inventor of the wrap dress, Diane von Fürstenberg had a keen eye for what made womenswear comfortable. Her personal life, including an early marriage to Prince Egon von Fürstenberg (pictured), meant that the two were often photographed—in this case in matching outfits.

Jane Fonda

Jane Fonda grew up in the spotlight (her father was Henry Fonda); she was free-spirited and politically active, and '60s street style photos captured her casual beauty, messy style (see also: her hair peeking out from under her cap and bare feet), and determination. Not much has changed on the latter front!

Bianca Jagger

If you're unfamiliar, Bianca Jagger was married to Mick Jagger until 1978; she was also a staple of the Studio 54 New York culture, so she was a '70s "party girl" icon. Pictured here in London in the late 1970s with her daughter, she didn't mind dipping into edgier trends (like menswear).

Cher

Even before street style became a way for public figures to debut new relationships, Cher had a profound understanding of how to use public awareness. Back when she was one half of "Sonny and Cher," the two wore matching outfits in everyday settings to emphasize their relatability, a must when you're a TV personality.

Farrah Fawcett

Most of Farrah Fawcett's "street style" and "naturalistic" photos were taken by fashion photographers or for promotional shoots of her on-screen work (for example, sitting on the ground in this casual photo). These images were an important part of her "girl next door" persona.

Blondie

As a continuation of the street style photography phenomenon in London, Debbie Harry (singer of the band Blondie) poses in the city, probably as part of a promotional shoot. The band was quite popular in England, and the city's vibe matched with Harry's feminine but incredibly edgy style.

Cyndi Lauper

Musicians made impressive use of street style photography to associate themselves with a particular ambiance or aesthetic. With the 59th Street Bridge behind her, it makes sense that the fashion-forward Cyndi Lauper attaches herself to New York City.

Madonna

Madonna embodied the more naturalistic parts of New York; here, she stands outside during the filming of Who's That Girl?, meaning that this is a combination between a production and a paparazzi photo. From the very beginning, her style and persona were an object of fascination, including her "off duty" outfits like this.

Princess Diana

Princess Diana was one of the most well-photographed women on Earth, but even more so post-separation and divorce from then-Prince Charles. During that time, she began to express her more casual side—including leaving the gym in bike shorts and sneakers, which remains as iconic today as it did then.

Kate Moss

Technically, this is a Calvin Klein photoshoot from their spring 1994 ready to wear collection, but the '90s ushered in a new synergy between celebrities and street style photography. Kate Moss and the "Big Six" were particularly photographed around town in their "off-duty model" style.

Carolyn Bessette-Kennedy

Some of the photos we have of Carolyn Bessette-Kennedy were unsolicited (to put it bluntly, the press hounded her during her relationship with John F. Kennedy Jr., and she wore neutrals to try and avoid attention), but her sense of simple, chic, high-low style was unparalleled—and she became inspiration for generations of women.

Julia Roberts

Celebrity airport style—aka, capturing public figures outside of the red carpet but still looking stylish as they headed to catch a flight—became more popular in the '90s. Here, Julia Roberts is headed to Los Angeles International Airport; her casual style was an important inspiration for the decade.

Courtney Love

There's a bit of a fine line between red carpet style and street style in this decade: case in point, this photo of Courtney Love, Kurt Cobain, and their new baby Frances (complete with baby bottle in Cobain's hand) en route to the MTV Video Music Awards.

Mariah Carey

In the '00s, street style was becoming a means of expression beyond debuting a cool outfit or looking incredibly relatable. It was also a way to push one's personal brand forward—and Mariah Carey, who went through a daring style evolution after her divorce from Tommy Mottola in the late '90s, was one of the first to do it.

Paris Hilton

Paris Hilton really leaned in on her party girl-fashion girl persona in this decade, further blurring the lines between fashion photography and paparazzi shots. Here, she poses at a Motorola event in her extremely '00s style (which, if you grew up in this decade, you'll remember well).

The Olsens

Street style photography could also establish someone as a more serious fashion force. Such was the case for Mary-Kate and Ashley Olsen, who retired from acting and started being photographed at fashion events and on the streets of New York as they founded luxury brand The Row.

Alexa Chung

If you've ever heard the words "fashion it girl," street style plays an important role in the development of said title. Alexa Chung has been a "fashion it girl" since the '00s, in part because her outfits at events—and walking on the street—established her as a person with highly covetable style.

Victoria Beckham

Victoria Beckham successfully transitioned her public profile from "former Spice Girl" to "serious fashion designer" by smartly being photographed in her own line, as well as other fashionable outfits—a strategy she continued doing, successfully, into the 2020s.

Chloë Sevigny

Chloë Sevigny achieved "it girl" status in the '90s and '00s, thanks to her acting but also her incredibly individual and eclectic style (in essence, her street style was one big exploration of "how is she pulling that off so well??"). Her career had a major resurgence in the 2020s and absolutely nothing changed about her aesthetic, in the most amazing way possible.

EmRata

Emily Ratajkowski has been an early forerunner of the "modern model street style." In other words, she would be "casually" photographed walking down the street in an incredible outfit, offering fashion inspo for us all and bringing a style of photography that was most often seen at fashion week arrivals, into everyday life. (Treat every day like it's a fashion week arrival, in other words.)

Jennifer Lopez

No one—no one!—has been better at using street style as an opportunity to share personal news than Jennifer Lopez. To be honest, she was treated pretty unfairly by the paparazzi in the '90s and '00s, but she turned it to her advantage by making street strolls and other public appearances. Her biggest relationship announcements have often been done via paparazzi photo!

Blake Lively

Blake Lively first became a street style phenomenon when she was photographed on set of Gossip Girl (wearing some very enviable fashion for its time). She continued that reputation in her later career, just with a more adult and colorful personal style.

Cardi B

Street style does not have to mean casual, and Cardi B is living proof of that. She's a mainstay at fashion shows and other appearances (here, she's outside Bravo Studios—in a couture gown). The street is her literal runway, and she's always giving 100 percent.

Hailey Bieber

Street style is endlessly self-referential, and modern street style pays homage to past iconic looks. For example: Hailey Bieber looks so much like Princess Diana here in an oversized sweater. She modernizes the look by skipping the visible shorts and wearing the sweatshirt like a dress.

Zoë Kravitz

As a descendant of celebrity royalty (Lenny Kravitz and Lisa Bonet), Zoë Kravitz probably has some impressive closets she can raid. But she's developed her own quirky, edgy aesthetic, and has become one of the best examples of modern celebrity street style.

Kendall Jenner

The modern-day supermodel takes the legacy of the '90s supermodel and iterates upon it. That includes street style, with Kendall Jenner strolling in Tribeca in a "casual" outfit that gives the rest of us major style envy and gives us a sense of how to wear a trending piece.

Rihanna

Pregnant ladies everywhere rejoiced when Rihanna stepped out with extremely modern maternity style—including a bare bump—that was in keeping with her aesthetic but adapting to her new status as mom-to-be. And her "mom of little kids" style has proven she hasn't lost her edge even a tiny bit.

Taylor Swift

No list of celebrity street style would be complete without Taylor Swift. When's she's photographed on the street, she simultaneously manages to debut a fashionable look, introduce or update us on her relationship status, lay out a few Easter eggs for hardcore fans, bring runway fashion into the everyday, and further her public persona. Incredible.