32 Classic Celebrity Street Style Moments

There's a lot to be said for celebrity red carpet fashion—but celebrity street style deserves its own moment. First popularized in the '60s (thanks to greats like Jane Birkin and Jean Shrimpton), the setting is simple: celebrities walking from one place to another in an effortlessly cool outfit. Next time you can't figure out what to wear, consider this your street style mood board.

Kim Kardashian

Kim Kardashian has a style that's all her own—and regardless of whether it's your particular cup of tea, you can't deny that it's fascinating to look at. These barrel jeans and over-the-top sunglasses are the perfect example: it's architectural and cool.

Jeanne Damas

If you're unfamiliar with French it-girl Jeanne Damas (she was in 2024's Becoming Karl Lagerfeld), her street style is a thing of beauty. She's got classic French style—like these tight ankle boots and classic slip skirt—with a touch of glamour and fun.

Camille Charrière

One of fashion's biggest influencers (as well as being a writer and editor), Camille Charrière has some of the most enviable looks—particularly during Fashion Weeks. This is one of her best, with the navy scarf and camel coat giving a perfect mix of casual-chic.

Elsa Hosk

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

Winnie Harlow

It would be incredible enough to be a top model, but Winnie Harlow also has fantastic everyday style that leans in on the couture. Dressing in head-to-toe Fendi (with no pants!) is a high degree of difficulty indeed, but she makes it look effortless.

Lucy Hale

Lucy Hale always looks incredibly polished—if you're unfamiliar, she's got great attainable style that you could easily emulate when you're running errands or headed to lunch. This all-white look with platforms is the perfect iteration of professional-but-relatable.

Drew Barrymore

The '90s saw a new side of Drew Barrymore that we immediately fell in love with: cool teen Drew, who didn't mind going casual at events. The leather jacket, white tee, black jean short, tights, and pretty berry-red lipstick: this wouldn't be out of place today!

Blake Lively

Blake Lively does glam extremely well (on the red carpet and otherwise), making good use of her long hair and 5'10" height. It might be difficult for most of us to pull off an all-orange pantsuit with strategically-placed cutouts, but our erstwhile Serena van der Woodsen makes it look easy.

Elle Fanning

Elle Fanning's been in showbiz since she was a literal child, so she's got a knack for styling herself in a way that's down-to-earth but still very, very polished. This simple beige coat and cropped jeans are elevated with pinch loafers and cool shades.

Zoë Kravitz

Zoë Kravitz has a lock on edgy, modern, deeply cool style. Somehow, she manages to look like the most interesting person in the room and also like she just threw on clothes from her (probably very enviable) wardrobe—or raided the closet of her two famous parents.

Winona Ryder

Winona Ryder in the '90s had a slightly grunge, slightly tough, but still quite feminine style (and this was even before she got her classic pixie haircut!). This is perhaps the most indelible image of her from that time, with her perfectly cuffed jeans and graphic tee.

Katie Holmes

Katie Holmes has been a street style darling for a long, long time, particularly in the late '10s and early '20s. During that time, her outfit choices were particularly surprising and bold: like the time she paired a white slip dress with Khaite animal print boots.

Kendall Jenner

Kendall Jenner has exceptional "model on the go" style—which means that if you care about fashion or trends, you keep an eye on her street style. Here, she's layering to perfection, and the surprising pop of color in her Gucci bag is the cherry on top.

Jennifer Aniston

Jennifer Aniston emerged from Friends as a '90s-'00s style maven, and she perfectly balanced romantic cuts and patterns with a more modern sensibility (as with this floral dress and nude strappy shoes)—not to mention that every single person wanted her hair.

Kaia Gerber

Street style can run in the genes, apparently. Kaia Gerber, whose mom Cindy Crawford became known for her off-duty model style in the '90s, became one to watch for her casual style two decades later. This one photo made everyone who saw it want to pair their floral skirts with Converses.

Sienna Miller

Sienna Miller has the kind of British it-girl style that has kept her a style inspiration for decades. She has an innate boho chic quality about her, which means that even when she's wearing a formal lace dress, she just brings a dose of casual cool.

Emily Ratajkowski

EmRata, as she's affectionately known, is often out and outfit in a casually flawless outfit. It makes sense, since she's a model and can make a lot of styles work for her, but there's also something about her poise and attitude (and in this case, cute dog) that makes it special.

Lupita Nyong'o

When Lupita Nyong'o first started hitting red carpets, it was with some of the most fabulous outfits and styling that we'd ever seen. That innate originality (including her love of color) has carried through to her casual street sightings and event-wear.

Cindy Crawford

It wouldn't be a list of best celebrity street style if Cindy Crawford weren't on here! Stars became known for their "airport style" in the '90s—it felt like a low-key version of their red carpet style—and Crawford was the queen of comfortable, functional, chic looks.

Naomi Campbell

On the opposite end of the spectrum, '90s-era supermodel Naomi Campbell was constantly giving us inspiration for a fun night out with girlfriends. Her ability to rock a minidress with tons of jewelry and some simple makeup was absolutely unparalleled.

Hailey Bieber

Honestly, this whole list could probably just be Hailey Bieber walking around the streets of New York in a great outfit. It's not just the designer brands she wears, although that's probably part of it: she also plays with structure, shape, and functionality in a way few celebs do.

Gisele Bündchen

Vogue called Gisele Bündchen's 2020s style "rich mom," and we can't disagree. She had a fashion comeback in 2023 that signaled her return to full-time modeling, and was quickly photographed in this incredible luxe coat, stiletto boot, cargo denim look.

Victoria Beckham

Victoria Beckham's transformation from Posh Spice to fashion icon was a joy to watch, and her street style outfits have been an important part of that. She often wears her own fashion line to slouchy perfection, not to mention some of the highest heels you've ever seen.

Kate Moss

Before she was the queen of festival style, Kate Moss was just an off-duty model giving us simple but incredibly cool style. The ripped tee and worn black boots contrast with the leopard handbag and chunky jewelry—but that's exactly what made Moss' looks so compelling.

Taylor Swift

No one has made street style work better for her than Taylor Swift. Her photo ops, whether she's at home in New York or (in this case) at a film festival wearing head-to-toe houndstooth, show how absolutely willing she is to try a new, fun aesthetic.

Gwyneth Paltrow

Gwyneth Paltrow just had an innate cool factor that many of us (myself included) tried in vain to replicate in the '90s. She singlehandedly made spaghetti strap tops and thin strap sandels seem like the coolest items of clothing—just like in this photo.

Rihanna

Over the years, Rihanna's style has evolved into casual-cool (and let's not even get started on how amazing her bump-baring maternity style was). She simultaneously looks like the most comfortable person in the room and the most interesting. She even makes sweatpants tucked into boots look chic!

Jean Shrimpton

Fun fact: street style (i.e., taking photos outside in a natural environment as you might find in real life) was not as 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.

Olivia Rodrigo

It's honestly so impressive that, given Olivia Rodrigo's age, how much the young singer-songwriter has become a fashion icon. From making use of impressive vintage gowns to popularizing her signature mini-and-chunky-shoes look, she never looks anything but perfect.

Margot Robbie

It makes sense that our modern Barbie would have 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 much cooler and more streamlined, with a lot of enviable pieces.

Meghan Markle

If you weren't tuned in while it was happening, it's hard to overstate the impressive impact Meghan Markle has made in fashion circles. When she and Prince Harry first started appearing together, like in this photo, her simple, chic, high-low style became everything.

Jane Birkin

Arguable, Jane Birkin (along with Jean Shrimpton) popularized street style before it was a thing. Even for photos that were clearly done by a professional, she exuded the kind of vibe that felt spontaneous and unconventional. Every photo of her is classic street style.