While there is much to be said for the attire of celebrities on the red carpet, celebrity street style also merits attention. It was first made popular in the 1960s by icons like Jane Birkin and Jean Shrimpton. The scene is straightforward: celebrities go between locations while wearing effortlessly stylish attire. Use this as your street style mood board the next time you’re stuck on what to wear.
Kim Kardashian
You cannot argue that Kim Kardashian’s style isn’t intriguing to look at, even if it’s not your specific cup of tea. The ideal illustration are these architecturally inspired and stylish barrel jeans and statement sunglasses.
Jeanne Damas
If you haven’t seen French it-girl Jeanne Damas (who starred in Becoming Karl Lagerfeld in 2024), her street style is stunning. With a dash of glitz and excitement, her typical French flair is evident in her tight ankle boots and slip skirt.
Camille Charrière
In addition to being a writer and editor, Camille Charrière is one of the largest figures in fashion, and she consistently pulls off the most lustful outfits, especially during fashion weeks. This is one of her best; the camel coat and navy scarf combine to create the ideal balance of casual and stylish.
Elsa Hosk
Even if Elsa Hosk’s tenure as a Victoria’s Secret Angel may be what most people know about her, you should nonetheless familiarise yourself with her street style. She always looks flawless, and she always follows the latest fashions, such as this long skirt and big jacket.
Winnie Harlow
Being a top model would be amazing in and of itself, but Winnie Harlow also has amazing everyday style that touches on couture. Although it takes a lot of work to dress entirely in Fendi (without trousers!), she pulls it off with ease.
Lucy Hale
If you’re not familiar, Lucy Hale always has an impeccable appearance. She has a terrific, approachable style that you could easily copy when you’re out to lunch or running errands. This all-white ensemble with platforms is the epitome of polished yet approachable style.
Drew Barrymore
We were instantly enamoured with a new side of Drew Barrymore during the 1990s: the cool young Drew who didn’t mind dressing casually at gatherings. The black jean shorts, tights, berry-red lipstick, white tee, leather jacket, and accessories wouldn’t look out of place today!
Blake Lively
Blake Lively is a master at glam, both on and off the red carpet, thanks to her long hair and 5’10” height. Most of us might find it challenging to style an all-orange pantsuit with well-placed cuts, but Serena van der Woodsen, our former model, makes it appear effortless.
Elle Fanning
Since Elle Fanning has been in the entertainment industry since she was a little child, she has a talent for dressing oneself in a way that is both casual and sophisticated. Pinch loafers and cool hues dress up this basic beige coat and cropped pants.
Zoë Kravitz
Zoë Kravitz is a master of the modern, edgy, and incredibly cool look. She somehow pulls off looking like the most fascinating person in the room and as though she just put on some outfits from her (likely much envied) wardrobe, or perhaps she raided the closet of her two well-known parents.
Winona Ryder
Even before she acquired her iconic pixie cut, Winona Ryder had a somewhat grungy, slightly rugged, but still very feminine style in the 1990s. Maybe the most memorable picture of her from that era is this one, wearing a graphic tee and nicely cuffed jeans.
Katie Holmes
For a very long period, especially in the late ’10s and early ’20s, Katie Holmes was a street style sensation. She made some really daring and unexpected fashion decisions during that time, such as the occasion when she wore Khaite leopard print boots with a white slip dress.
Kendall Jenner
Because of her amazing “model on the go” approach, Kendall Jenner is someone to watch whether you’re interested in trends or fashion. She’s layering this perfectly, and her Gucci bag’s unexpected flash of colour is the icing on the cake.
Jennifer Aniston
After leaving Friends, Jennifer Aniston became a style icon of the ’90s and ’00s. She skilfully combined romantic cuts and patterns with a more contemporary sensibility (see this floral dress and nude strappy shoes), and not to mention, everyone wanted her hair.
Kaia Gerber
It seems that street style can run in the family. Two decades later, Kaia Gerber—whose mother Cindy Crawford rose to fame in the 1990s as an off-duty model—became a style icon due to her easygoing look. Everyone who viewed this one picture was inspired to wear Converse trainers with their flowery dresses.
Sienna Miller
For many years, Sienna Miller has served as a style icon thanks to her quintessential British look. She merely adds a touch of casual cool, even when she’s dressed in an elegant lace dress, because she exudes an inherent boho chic quality.
Emily Ratajkowski
EmRata, as she is often called, is frequently spotted out and about wearing effortlessly stylish clothing. It makes sense because she’s a model and can pull off a multitude of looks, but it’s also unique due to her elegance, attitude, and, in this case, her adorable puppy.
Lupita Nyong’o
Lupita Nyong’o wore some of the most amazing dresses and styling we had ever seen when she first began appearing on red carpets. Her natural creativity (which includes her love of colour) is evident in the informal street sightings and event attire she chooses.
Cindy Crawford
Without Cindy Crawford, this list of the greatest celebrity street style wouldn’t exist! In the 1990s, celebrities developed a “airport style” that was akin to a more subdued version of their red carpet looks. Cindy Crawford was the epitome of the effortlessly stylish yet comfortable look.
Naomi Campbell
Conversely, supermodel Naomi Campbell of the 1990s was a continual source of inspiration for enjoyable evenings spent with friends. She had the most amazing ability to look effortlessly put together in a minidress with lots of jewellery and minimal makeup.
Hailey Bieber
Sincerely, this entire list might just be Hailey Bieber strolling through New York City while stylishly dressed. Though that certainly plays a role, it’s not just about the high-end labels she dons; she also experiments with form, structure, and usefulness in a manner that very few celebrities do.
Gisele Bündchen
We don’t disagree that Gisele Bündchen’s 2020s fashion was dubbed “rich mom” by Vogue. In 2023, she made a fashion statement that announced her return to full-time modelling. She was soon seen on camera looking stunning in a luxurious coat, high-heeled booties, and cargo jeans.
Victoria Beckham
It was entertaining to observe Victoria Beckham’s transition from Posh Spice to fashion icon, and her street style ensembles played a significant role in that. She frequently sports some of the tallest heels you’ve ever seen in addition to her own fashion line, which she wears to slouchy perfection.
Kate Moss
Kate Moss was only an off-duty model who gave us basic yet really cool style before she became the queen of festival style. The leopard purse and oversized jewellery clash with the torn t-shirt and old black boots, but that’s precisely what made Moss’s looks so alluring.
Taylor Swift
Nobody has done a better job of enhancing her street style than Taylor Swift. Her photo ops demonstrate how eager she is to try out a fresh, playful look, whether she’s at home in fresh York or (in this example) at a film festival and are dressed entirely in houndstooth.
Gwyneth Paltrow
I, like with many others, attempted in vain to emulate Gwyneth Paltrow’s natural coolness in the 1990s. Like in this picture, she was the only one who could make spaghetti strap blouses and thin strap sandals seem like the greatest things to wear.
Rihanna
Rihanna’s style has changed throughout time to become more casual-cool (and let’s not even talk about how beautiful her bump-baring pregnancy style was). She appears to be the most intriguing person in the room and the most at ease at the same time. She even looks stylish when wearing sweatpants tucked into boots!
Jean Shrimpton
Fun fact: street style, or photographing pictures outside in real-world settings, was not as common until the 1960s, when Jean Shrimpton and photographer David Bailey made it famous. She’s someone you should add to your Pinterest board if you enjoy that decade’s fashion.
Olivia Rodrigo
Given Olivia Rodrigo’s age, it truly is astounding how much the young singer-songwriter has grown to become a style icon. She always looks flawless, whether it’s by rocking stunning vintage outfits or making her typical mini-skirt and chunky shoes seem fashionable.
Margot Robbie
It makes natural that the great red carpet style of our modern Barbie would be (often) pink. You may not be aware of this, but Robbie also has a street style that showcases a distinct aspect of her personality. It’s far sleeker, cooler, and full of pieces that would make any fashionista jealous.
Meghan Markle
The enormous impression Meghan Markle has made in fashion circles is difficult to overestimate if you weren’t paying attention when it was occurring. Her effortless, sophisticated, high-low style became the talk of the town when she and Prince Harry made their public debuts together, as shown in this picture.
Jane Birkin
Perhaps more than Jean Shrimpton, Jane Birkin popularised street style before it was a thing. She had that air of spontaneity and unconventionality, even in shots that were obviously taken by a professional. She always looks great in street photos.
