32 Classic Celebrity Street Style Moments

32 Classic Celebrity Street Style Moments

Celebrity red carpet fashion has much to offer, but celebrity street style also has its own value. First popularized in the 60s (thanks to greats like Jane Birkin and Jean Shrimpton), this style is simply celebrities walking from place to place in effortlessly cool attire. When you're not sure what to wear next, take a look at this street-style mood board.

There's no denying that Kim Kardashian has a style all her own, and whether it's to your taste or not, it's a sight to behold. These barrel jeans and over-the-top sunglasses are a perfect example.

If you're not familiar with French It Girl Jeanne Damas (she was in 2024's Becoming Karl Lagerfeld), her street style is the epitome of beauty. Classic French styles, like tight ankle boots and classic slip skirts, are infused with glamour and playfulness.

Camille Charrière, one of fashion's biggest influencers (as well as a writer and editor), has some of the most enviable looks, especially during fashion week. This is one of her best, with the navy scarf and camel coat the perfect mix of casual chic.

You may be most familiar with Elsa Hosk from her days as a Victoria's Secret Angel, but you should also know her street style. She's always impeccably put together and embraces fun trends (including this oversized jacket and maxi skirt).

Being a top model is amazing enough, but Winnie Harlow also has a great everyday style that leans more towards couture. It's a real challenge to dress head-to-toe in Fendi (no pants), but she pulls it off effortlessly.

Lucy Hale is always amazingly sophisticated - if you're not familiar with her, she has a great, attainable style that is easy to copy when running errands or heading out to lunch. This all-white look and platform is the perfect iteration of professional yet approachable.

The 90s saw a new side of Drew Barrymore that we immediately fell in love with: as a cool teen, Drew didn't mind going casual at events. Leather jacket, white T-shirt, black jean shorts, tights, berry red lipstick.

Blake Lively is very good at dressing glamorous (on the red carpet or otherwise), taking advantage of her long hair and 170cm height. Wearing an orange pantsuit with strategically placed cutouts may be difficult for most, but the former Serena Van Der Woodsen pulls it off with ease.

Elle Fanning has been in showbiz since she was literally a kid, so she knows the knack of styling in a way that is down-to-earth yet very sophisticated. This simple beige coat and cropped jeans are elevated with pinch loafers and cool shades.

Zoë Kravitz rocks an edgy, modern, deeply cool style. Somehow, she manages to look like the most interesting person in the room and at the same time look like she just threw on some clothes from her own (probably very enviable) wardrobe or raided the closets of her two famous parents.

Winona Ryder in the 90s was a little grungy, a little tough, but still quite feminine (this was before she went for the classic pixie hair). This is perhaps the most unforgettable image of her at the time, wearing perfectly cuffed jeans and a graphic T-shirt.

Katie Holmes was a street style darling for a long time, especially in the late teens and early 20s. Like when she wore a white slip dress with animal print boots by Kaite.

Kendall Jenner has an outstanding "model-on-the-go" style - which means if you care about fashion and trends, keep an eye on her street style. Here, she shows off the perfect layering and accents it with an unexpected pop of color from her Gucci bag.

Jennifer Aniston emerged from "Friends" as a style maven of the '90s and '00s, perfectly balancing romantic cuts and patterns with a more contemporary feel (like this floral dress and nude strappy shoes).

Street style is apparently in the genes. Kaia Gerber, whose mother Cindy Crawford became known for her off-duty modeling style in the 90's, became noticed for her casual style 20 years later. Everyone who saw this one photo wanted to pair it with a floral skirt and converse.

Sienna Miller has a kind of British it-girl style that has remained a source of style inspiration for decades. She has innate Boho chic qualities, and even when she wears formal lace dresses, she still manages to look casual and cool.

Nicknamed Emrata, she often goes out dressed casually and impeccably. That makes sense since she is a model and can wear many styles well, but her attitude and demeanor (and in this case a cute dog) make her special.

When Lupita Nyongo first appeared on the red carpet, it was the most amazing outfit and styling we had ever seen. Her innate originality (including her love of color) carried over to her casual street sightings and event wear.

It wouldn't be a Best Celebrity Street Style list without Cindy Crawford here; in the 90s, stars became known for their "airport style," which looked like a low-key version of red carpet style and Crawford was the queen of the comfortable, functional, chic look.

Conversely, 90s supermodel Naomi Campbell was a constant source of inspiration for a fun night out with girlfriends. Her ability to rock a mini dress with tons of jewelry and simple makeup was absolutely unmatched.

Honestly, this entire list could just be Haley Bieber walking the streets of New York City looking fabulous. It's not just the designer brands she wears, although that may be a factor.

"Vogue" called Gisele Bundchen's 2020s style "Rich Mom," and we wouldn't disagree. She made a fashion comeback that signaled her return to full-time modeling in 2023, and was immediately photographed in this incredible luxe coat, stiletto boots, and cargo denim look.

Victoria Beckham's transformation from posh spice to fashion icon was fun to watch, and her street-style outfits were an important part of it. She often wears her own fashion line slinkily and flawlessly, not to mention the tallest heels you've ever seen.

Before becoming the queen of festival style, Kate Moss was just an off-the-cuff model, showing us her simple but incredibly cool style. Torn T-shirts and worn black boots contrasted with leopard handbags and chunky jewelry, but that's what made Moss' look so compelling.

No one wears street style better than Taylor Swift. Whether at home in New York or at a film festival in head-to-toe staggered outfits, her photoshoots show how absolutely willing she is to try new and fun aesthetics.

Gwyneth Paltrow had an innate cool factor that many of us (myself included) tried in vain to replicate in the 90s. She single-handedly made a spaghetti-strapped top and thin-strapped sandals seem like the coolest item of clothing, as shown in this photo.

Over the years, Rihanna's style evolved into casual cool (and let's not even mention how great her bump-baring maternity style was). She simultaneously looks like the most comfortable and most interesting person in the place. Even her sweatpants-in-boots look chic.

Fun fact: street style (i.e. This style wasn't that popular until Jean Shrimpton and photographer David Bailey popularized it in the 60s. If you like the style of that decade, she's one to add to your Pinterest board.

Considering Olivia Rodrigo's age, it is honestly quite impressive that this young singer-songwriter has become a fashion icon. From utilizing striking vintage gowns to popularizing her signature mini and chunky shoe look, she is nothing short of perfection.

It makes sense that the modern Barbie has excellent (often pink) red carpet style. But what you don't know is that Robbie also has a street style that expresses a different side of her personality. [It's hard to overstate the impressive impact Meghan Markle has had on the fashion world. Her simple, chic, high-low style became everything when she and Prince Harry first appeared together, as seen in this photo.

It is indisputable that Jane Birkin (along with Jean Shrimpton) popularized street style before it was fashionable. Even in her obviously professional photographs, she exuded an air of spontaneity and unconventionality. All of her photos are classic street style.

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