These celebrities dared to dress down for the red carpet - and still looked amazing
Designer gown at the dry cleaner? These celebrities swapped typical red carpet glam for dressed-down street style
As they say, there can be too much of a good thing - and for celebrities, the allure of the glamorous red carpet might get tiring after a while.
Which is why it's refreshing to see some of the biggest stars turn up dressed down or in more relatable, easy-to-repeat street style looks.
Whether it's jeans and a nice top (a classic!) or elevated everyday basics, these stars make a serious case suggesting that less sometimes really is more.
32 times celebrities brought street style to the red carpet
Sarah Jessica Parker, 1992
Back in the early 1990s, Sarah Jessica Parker was years away from stepping into the (always fabulous) shoes of her most defining character, Carrie Bradshaw.
But that didn't mean the actress wasn't already applauded for her own fashion acumen. The First Wives Club star stepped out for a Los Angeles movie premiere wearing a very-90s minimalist outfit, dressing down in a relaxed, monochrome white outfit.
Pairing a tighter, cropped tee with a flowing maxi skirt was an excellent way of styling the one-colour outfit, and stopped her petite frame from being swallowed up.
Meg Ryan, 1999
Low-key but still lovely, Meg Ryan showcased how to do red-carpet fashion without all the fuss for the 1999 Golden Globe Awards.
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The actress - beloved for being involved in some of the most memorable rom-com lines of all time - paired a rather subdued and formal-looking grey knit top with a flowing, pastel yellow maxi skirt. The unusual contrast was a fun way of playing with texture and shape.
Drew Barrymore, 1991
Drew Barrymore has lived a few lives in her decades-spanning career, and in the 1990s, she was very much in a more bad-girl, grunge phase.
In 1991, she eschewed the usual red carpet pressures and rocked up with ripped jeans, a short-fitting button-up sweater and messy hair. It was the 90s. Not caring was very chic.
Salma Hayek, 1999
Salma Hayek always looks glamorous - her best fashion moments prove that she pretty much is incapable of looking bad.
But ditching her trademark body-hugging dresses in 1999, Salma attended the premiere of Eyes Wide Shut wearing a fun and flirty printed cropped shirt - exposing enough of her toned midriff to be daring but not excessive - with a matching bandana.
Matching the orange print shirt, she wore a full-length brown leather skirt.
Jada Pinkett Smith, 1999
With the red carpets now more of a parade of designer, you tend to forget they used to be a great way for celebrities to showcase their own personalities.
Looking playful and sexy, Jada Pinkett sported a cropped black tee with western-themed leather trousers (complete with fringe down the seams) for the 1999 premiere of Will Smith's Wild Wild West.
Jada was having fun with the western theme, accessorising with a cowboy hat.
Reese Witherspoon, 1999
Reese Witherspoon attended the 1999 premiere of Cruel Intentions dressed casually but still looking on trend for the era.
Keeping a simple, white shirt as a focal point, the bottom of her flowing magenta maxi skirt and gold ribbon tied around the waist allowed for pops of colour to inject some fun without becoming too much.
Jennifer Aniston, 1998
While many celebrities must love getting to dress up for red carpets these days, there are probably just as many who miss the days when you could rock up in a nice top and a pair of jeans.
And based on every time we've seen Jennifer Aniston make a t-shirt and jeans her go-to look, she's high on that list.
Jen attended a film premiere in 1998 wearing a pair of slouchy blue jeans and a navy v-neck shirt. Looking understated, her hair was down in her trademark beachy waves and she wore a pair of open-toe wedges.
Gwyneth Paltrow, 1996
Looking part Catwoman and part any corporate working girl in the 2020s, Gwyneth Paltrow's 1996 casual style was both timeless and very on trend for recent years.
Wearing a high-necked, tight black top and a pair of skin-tight leather black jeans, she mastered a sense of high-low. Her look wouldn't look out of place in a swanky working space or at cocktails in the city.
Christina Aguilera, 1999
While multiple pieces of animal print and a short skirt might sound crazy for some, for a 1990s Christina Aguilera, this was practically demure.
The Genie in a Bottle singer looked youthful and on-brand at the 1999 MTV Video Music Awards, pairing a semi-sheer leopard print camisole with a matching leopard print overcoat.
The simple black skirt and boots kept the look from becoming too loud and allowed the leopard print to be the focal point.
Sarah Jessica Parker
Ever wondered what Carrie Bradshaw would look like if she ditched Mr Big for a biker and swapped her best looks for something more rough and tough?
Well, SJP gave a window into what might have been when she stepped out of her style comfort zone in an oversized leather jacket, black mini dress and chunky biker boots.
She even went for a darker look around her eyes than we'd come to expect from the stylish Sex and the City star.
Gwyneth Paltrow (and a bonus Brad Pitt)
We have not one, but two, dressed down, street-style stars as the former, short-lived Hollywood It Couple stepped out in matching casual attire.
Brad Pitt - wearing a sweater vest and relaxed trousers - matched his then-girlfriend, Gwyneth Paltrow's chill vibe, as she swapped usual red carpet glamour for a loose, full-length cotton white dress.
The pair's matching sunglasses gave them a touch of that Hollywood star power, though.
Jennifer Lopez, 1998
Jennifer Lopez's best looks over the years are packed full of the sequinned and sexy luxury that's become her signature, but back in 1998, she kept things more low-key and street-style adjacent.
Supporting the premiere of Ben Affleck's Armageddon, JLo kept things simple but still fresh, pairing a pair of cropped black trousers with a matching jacket and a cropped white top. A pair of sunglasses and some strappy stilettos gave the black-and-white look a sense of elevated glamour.
Penelope Cruz, 1999
Academy Award-winning actress Penelope Cruz always brings glamour to the red carpet, but back in 1999, she kept things more understated.
The Vanilla Sky star stepped onto the red carpet wearing a patterned poncho and a pair of blue jeans.
Dressed down but still stylish, Penelope matched the colours in the poncho's design with her jeans and her darker lip colour.
Courteney Cox, 1995
Friends icon Courteney Cox kept things fun and flirty for the 1995 MTV Movie Awards, while still dressing more casually and of the time.
Instead of a designer gown, Courteney flashed her toned stomach in a cropped shirt with statement, flowing sleeves. Paired with a pair of tailored navy trousers and strappy white wedges, it's a look that wouldn't be out of place at a daytime event today.
Tyra Banks, 1997
Even supermodels weren't immune from ditching traditional glam for street-style cool and relatable trends in the 90s.
Tyra Banks attended a film premiere in 1997 looking like she'd just finished doing chores around the city. In a pair of Adidas sliders, light-blue denim jeans, a simple white tee and even lugging around a tote bag, fashion and function came together on that red carpet.
Kate Winslet, 1996
Titanic star Kate Winslet attended the Golden Globes in 1996 in a sleek ensemble that would've been a great day-to-night street-style set for the time.
With statement outerwear, Kate could keep the look unfussy, choosing to keep her shiny, cobalt blue trench coat the eye-catching foundation of the outfit. She paired it with a pair of simple navy trousers and kept her glam simple, with messy hair and natural makeup.
Julia Roberts, 1993
We've seen the Pretty Woman star live up to her reputation as one of Hollywood's last true movie stars with her best looks over the years, but Julia Roberts also liked to keep things casual and laid back in the 90s.
In 1993, she pulled off something of a fashion faux pas, mixing horizontal stripes with vertical stripes. Of course, she looked effortlessly chic doing so, with the tight, cropped tee and baggy trousers showcasing her tall, slim frame.
Cameron Diaz, 1998
Charlie's Angels star Cameron Diaz chose an unconventional look back in 1998, playing with a few different street-style trends.
Heavy outerwear and statement coats were a thing in the late 90s, with plenty of Hollywood stars choosing to wear oversized coats and suit jackets. Cameron paired her heavy-duty grey coat with a bright red scarf.
Perhaps in contrast to the engulfing, dark coat, Cameron also added a jaunty hat and bright blue eyeshadow.
Rose McGowan, 1998
Rose McGowan's 1998 red carpet look was somehow both simple and statement-making.
Essentially, it was just a jumper and trousers. But Rose added some personality to the simple styling, introducing both colour and textures. The jumper was a glittery pink, while the black leather trousers gave a contrasting rock edge.
The addition of a lime green fluffy scarf made this look one that you'll either love or hate.
Sandra Bullock, 1999
For the 1999 premiere of her movie, Forces of Nature, Sandra Bullock looked chic and glamorous without relying on anything too OTT.
The stylish star pulled off a monochrome look in a warm, burgundy hue, pairing a simpler sleeveless, scoop-neck top with a silky-looking maxi skirt or sarong.
Gwyneth Paltrow
While it seems getting red carpet-ready today is a whole day affair, there was something in the air in the 90s that felt like celebrities simply popped along after doing something else.
Gwyneth Paltrow turned up for an appearance wearing a simple black co-ord set and threw on a statement leopard print coat over the top. The mix of loud print with a simple set underneath is a masterclass in how to easily elevate a last-minute look.
Nicole Kidman, 1996
Nicole Kidman is always one of the best-dressed stars, someone who takes the same risky swings with her fashion choices as she does her film roles. And that's why people can't wait to see what she wears when she appears.
In the 90s, Nicole was the ultimate cool girl, wearing street-style casuals in a way that felt elevated.
In 1996, when she was still with Tom Cruise, she joined him for the premiere of one of his movies. Keeping things effortlessly cool, Nicole wore a floor-length, button-up dress with a matching jersey headband.
Madonna, 1999
The 1999 Grammys were a big one for the Queen of Pop, but Madonna kept her outfit rather casual and cool.
Picking up three Grammys on the night, Madonna's street-style inspired outfit put plenty of attention on the embroidered, patterned jeans, pairing them with a simple white vest top (which had the added bonus of showcasing her impressively toned arms!).
Uma Thurman, 1997
Uma Thurman looked street-style cool in 1997 when she rocked the red carpet wearing a baggy dress cinched in with the most 90s of additions - a jumper fastened around the waist.
Cher, 2000
From her daring Bob Mackie Oscars ensemble, which totally went against the dress code to her genre-defying career, Cher has never been one to really care about the rules.
This is why street style on the red carpet just makes total sense for the icon. Rocking the red carpet in 2000 completely uninterested in dressing up in stereotypical fashion, Cher also didn't seem interested in being accused of committing the fashion faux pas of double denim.
Katie Holmes, 2022
Many of the street-style inspired looks on the list hail from the 90s, when red carpets followed a different set of rules. And that's why it's even more impressive that actress Katie Holmes dared to dress down for an appearance in 2022!
Keeping to the foolproof code of 'jeans and a nice top', Katie attended the iHeartRadio Jingle Ball wearing what appears to be a mini navy dress as a top, over a pair of baggier blue jeans.
Cameron Diaz, 1996
Cameron Diaz's 1996 red carpet look is surprisingly laid back and easy to recreate due to its timelessness.
With a flattering pair of tailored trousers in a nice colour (Cameron went for a maroon-y hue), a simple top and a cardigan in a fun print - like Cameron's leopard - you have an outfit that you can throw together in minutes which doesn't look low effort.
Olivia Rodrigo, 2023
One of the rising stars of the new generation, Olivia Rodrigo has conquered TV and music - and she's well on her way to becoming a fashion icon too.
Daring to do things a little differently, the star stepped out in a surprisingly dressed-down look for 2023's Billboard Women in Music, wearing a pair of flared trousers featuring a pattern on the side and a simple brown leather tube top.
Nicole Kidman, 2000
Oscar-winning icon Nicole Kidman kept things fun and relaxed in 2000 when she supported her then-husband Tom Cruise's Mission Impossible II premiere.
Nicole wore a sleeveless, high-neck halter top in a gold print with a pair of simple black trousers. Allowing the gold to stand out, she kept her accessories on theme, with gold bangles.
Madonna, 2016
Madonna's street-style look in 2016 was a masterclass in mixing high and low concepts.
The Like a Prayer star swapped her usual provocative looks for a relaxed, streetwear-inspired varsity jacket dress. Keeping with the street style vibe, she added large gold hoop earrings.
However, for some vintage glamour vibes, Madge wore a towering pair of patent black leather heeled boots.
Shania Twain, 2019
How do you take a signature look and keep it consistent even when you want to keep things more simple or street-style inspired?
Well, if you're Shania Twain, you take your trademark leopard print style and weave it into a very simple silhouette. Shania looked on-brand and stylish in a deceptively easy look, wearing a silky leopard shirt with a pair of black skinny jeans.
Jlo, 1999
Jenny from the Block knows how to take street style and elevate it for a glam red carpet appearance.
The singer-dancer-actress gave two street-style staples - a halter neck and jeans - a classic JLo twist in 1999, making them both a coordinated explosion of sequins.
Keeping to the bold and bright theme, Jennifer switched her usual soft glam for silvery, smoky eyes.
Jack Slater is not the Last Action Hero, but that's what comes up first when you Google him. Preferring a much more sedentary life, Jack gets his thrills by covering news, entertainment, celebrity, film and culture for woman&home, and other digital publications.
Having written for various print and online publications—ranging from national syndicates to niche magazines—Jack has written about nearly everything there is to write about, covering LGBTQ+ news, celebrity features, TV and film scoops, reviewing the latest theatre shows lighting up London’s West End and the most pressing of SEO based stories.
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