Looking at red carpet photos from any given year transports you back in time, allowing you to recall the biggest celebrities, major trends, and, in some cases, even the most pressing issues on people’s minds. The awards season is the most exciting season of the year. As the season begins, we are rewarded for our devotion to pop culture by watching movies, listening to music, and obsessing about television. Every star was once a newbie on the red carpet, whether they were an instant sensation or had to work hard for years before their big breaks and hard-earned credits. When our favorites win, we shed tears of joy, and when the results aren’t in our favor, we scream. But we all know that half the fun of award season is seeing what celebrities wear on the red carpet. Would they go for a classic look? Maybe they’ll do something amusing with the current fads? What are we supposed to expect from Lady Gaga? Ahead, we’ve compiled a list of our favorite red carpet appearances by Hollywood’s biggest names.
Tyra Banks
Tyra Banks is one of the most well-known fashion models, and of course, she’s walked the red carpet all the time. The supermodel, who rose to fame in the 1990s alongside Claudia Schiffer and Amber Valletta, has pushed the industry’s limits. In addition to her credit, she is also the creator of the television phenomenon known as America’s Next Top Model. Banks showed us all about the “booty tooch” and “smize” on the reality competition show.
In 1994, Banks appeared in a shimmering blue dress at the Council of Fashion Designers of America (CDFA) Awards in New York City. She made an appearance on the red carpet at the 26th annual NAACP Awards in the same year. She still knows how to make a statement on the red carpet, and she did just that at the 2019 American Music Awards red carpet. In a brown pantsuit, Banks dazzled on the red carpet. Her black bra was visible under the jacket portion of the pantsuit, which was left unbuttoned. Tyra completed her ensemble with a white hat and black leather gloves.
Taylor Swift
Taylor Swift is not only a music hero, but she’s also a total fashion icon! She first walked a red carpet when she was 16 years old, in 2006. Take a moment to process that information. There’s a lot of fashion to unpack here, from her country days wearing cowboy boots with minis to her sparkly pop queen looks.
Swift, a rising country star, debuted her single Tim McGraw in her credit, which hit the top ten on Billboard’s Hot Country chart in 2006. She matched her cute heels with a white dress with black western-style accents. The tresses! Nashville’s allure! And, of course, the cowboy boots!!! It was Taylor’s first performance at the ACMs, and she went on to win Top New Female Vocalist the following year. Swift made her most recent appearance in 2020, attending the Sundance Film Festival premiere of Miss Americana in a Carmen March jumpsuit with a matching coat draped over her head, looking like the coolest girl boss.
Serena Williams
Serena Williams has perfected the art of dressing for the red carpet over the years, as well as her inimitable approach to on-court style as her strong serve. Williams wears sky-high stilettos and replaces her neon tennis sets with similarly bright body-con dresses when she’s not in her sneakers – or her warrior-Esque knee-high Nike boots.
Her style was characterized by slinky wrap dresses and form-fitting strapless gowns in the Noughties, and more recently, slinky wrap dresses and form-fitting strapless gowns. She swapped her Wimbledon whites for a frothy Oscar de la Renta gown for the 2011 Met Gala. Serena Williams wowed in a sunshine-yellow Atelier Versace gown paired with Off-White x Nike sneakers at last year’s camp-themed affair. To her credit, her red-carpet style is as bold as her forehand winners elsewhere. She walked the red carpet at the 2019 Oscars in a figure-hugging, strapless custom Armani Privé gown with a slick ponytail and gleaming jewels.
Scarlet Johansson
Scarlett Johansson, who has been in the spotlight since she was a child, embraced Old Hollywood glamour early on. Scarlett Johansson’s style has evolved, from pantsuits to Preen, but one thing has remained consistent: the actress still looks supremely sophisticated on the red carpet. Whether she’s channeling Old Hollywood glamour in a figure-hugging gown or going modern in quirky Rodarte, Johansson pulls off every look with ease and confidence. The actress has recently taken a more mature approach to her wardrobe, favoring formal, metallic gowns, chic suits, and tailored separates.
Oscar de la Renta is no stranger to the Academy Awards, so it’ll come as no surprise to see the mark on a few celebrities at the 2020 Vanity Fair Oscar Party. On the red carpet of the 2020 Oscars, the actress received reviews for her ODLR gown to her credit. There was a feeling of edgy allure with a peek-a-boo cutout framing her ribcage tattoo, which brought this from old to new Hollywood while also retaining modern elegance.
Sarah Michelle Gellar
Sarah Michelle Gellar is reminiscing about her youth. In honor of the 2018 Emmy Awards, the Buffy the Vampire Slayer star donned her “favorite dress,” which she wore to the 1999 Emmy Awards and still fits!
On her Instagram Story, the Buffy the Vampire Slayer actress flaunted her slender figure in the blue gown she wore to the Emmy Awards 19 years ago. She accessorized her Vera Wang gown with brown UGGs and the Emmy award she received that evening. Fans were astounded to see the actress wearing the same dress after so many years, particularly because she has had children since then. In 2014, Gellar spoke about her biggest — and cutest — fashion critic, as well as how she prioritizes comfort over style when it comes to her own. The star is definitely making fashion investments in both comfort and style.
Sarah Jessica Parker
Sarah Jessica Parker’s flawless personal style cemented her reputation as a fashion icon, despite the fact that she was made famous by the Manolo-obsessed Carrie Bradshaw. Her accomplishments as an actress have been credited with numerous nominations and awards, including Golden Globes, Emmys, Screen Actors Guild Awards, and, most recently, a People’s Choice Award for her role in the television series Divorce.
Parker is known for choosing fashion with a capital F on the red carpet, opting for up-and-coming designers and over-the-top couture looks that most other Hollywood actresses would avoid. Parker attended a movie premiere in Los Angeles in 1991 wearing red velvet jeans, a gold bra hidden by a patterned jacket and isn’t afraid to reveal any skin. Parker wrapped herself in a gilded production by Dolce Alta Moda that was covered in precious stones in 2018, completely committing to the year’s “Heavenly Bodies” theme. She also wore a larger-than-life Neapolitan nativity scene on her head. Speak of a crowning moment.
Sandra Bullock
Award-winning actor On the red carpet, Sandra Bullock has always made a point. It’s hard to recall a time when the actress wasn’t America’s sweetheart—with a wardrobe full of Lanvin and Marchesa to match—but after more than two decades on the red carpet, she’s tried it all: crop tops, plunging necklines, even frosty lipstick (it was the ’90s, after all).
Sandra Bullock made her film debut 30 years ago, in the 1987 thriller Hangmen, in a minor role. She went on to receive an Academy Award, two Screen Actors Guild Awards, and a Golden Globe, among several other credits, over the next several decades. Bullock stunned in a shimmering champagne-hued Marchesa gown when she won Best Actress in 2010; four years later, when she was nominated again, this time for her role in Gravity, she chose a much more subtle number, a strapless navy mermaid gown by Alexander McQueen. The actress is also not afraid to wear bold colors, as evidenced by her violet Bottega Venetta gown from the 2010 Golden Globes and a Prabal Gurung color-blocked gown from the 2014 event.
Rihanna
Rihanna has been a style favorite at premieres, concerts, and award shows since her debut in 2005. Fans and fashionistas alike still look forward to seeing what the Bajan beauty will wear, and with good reason: no one rocks the red carpet like Bad Gal RiRi.
Rihanna’s style has influenced countless column inches over the years, more so than ever since she turned her love of fashion and beauty into a lucrative Fenty empire, putting aside her (many) musical credit and accomplishments. Rihanna is without a doubt her own best advertisement – she’s rarely seen without a Fenty trophy piece or two on her person – but she also proudly wears clothes that aren’t her own. In 2019, Rihanna wore a vintage John Galliano spring/summer ’95 dress with black strappy sandals, a satin clutch, and layered jewelry to the premiere of Lena Waithe’s Queen and Slim.
Penélope Cruz
Penélope Cruz has ascended to the ranks of Hollywood royalty. As award season arrives, it’s almost a given that she’ll walk the red carpet looking as stunning as ever. Not to mention, she’ll be dressed by some of the world’s most prestigious designers. When she wears one of her stunning gowns, all eyes are on her. The Spanish actress is known for her timeless elegance, which complements her sleek and sophisticated sense of style.
To her credit, she is often cited as one of the best dressed on the red carpet events she attends. In fact, her look at the 2007 Academy Awards will go down in history as one of the best Oscar looks ever. In case you’re wondering what happened back then, Penélope wore an Atelier Versace gown that was flawless in every way. The bodice was a great match for her if you ask us. The gown’s color complimented her olive skin, and the intricate feathered train added a lot of flair to the outfit. In January 2020, Penélope attended the 92nd Annual Academy Awards, looking as stunning as ever. She was dressed in a lovely black gown with a halter neck and a flower in the middle, which added a splash of color to the otherwise dark outfit.
Pamela Anderson
Pamela Anderson is credited for her bleached blonde hair, curvy figure, and dramatic eye make-up. Pammie’s signature look lasted for nearly two decades, but she’s finally broken out of her beauty style rut and seems to have come full circle. Her hair, make-up, and wardrobe have been softened to a level we haven’t seen since she first appeared on our screens in the early 1990s.
Anderson wore a plain white gown to the Vanity Fair Oscar Party in 1999, which was more provocative than her previous looks but still toned down from most of her late-’90s wardrobe. While she rocked her iconic heavy dark eye make-up for years, the 49-year-old recently ditched her signature look. Pamela Anderson returned to the Westwood Fashion Week circuit in March 2017. In a sequined gown, the actress stole the spotlight from Kelly Rohrbach at the world premiere of the Baywatch reboot in South Beach in the same year.
Oprah Winfrey
Oprah Winfrey has always had a fiery personality and an equally fiery personal style. Winfrey has established herself as a red carpet regular, gracing award shows and premieres with her own brand of glitz. The actress has gravitated toward some pretty daring looks since the beginning of her career. Shoulder pads, designs, and glistening embellishment were all the rage in the 1980s. We saw the star wear a degree of monochromatic looks in the 1990s and 2000s that were just as striking. It’s also worth noting that the Queen of All Media knows how to work a red carpet gown.
She has an eclectic designer palette, with Azzedine Alaia, Vera Wang, Victoria Beckham, and Atelier Versace all making appearances over the years. The renowned talk show host is undeniably devoted to Stella McCartney’s designs. In fact, she chose a piece by the designer for Prince Harry and Meghan Markle’s 2018 wedding.
Nicole Richie
Nicole Richie has gone through several changes during her time in the spotlight, from rock royalty to reality star, from It Girl to fashion designer in her own credit. One thing hasn’t changed, though: she’s a style icon who exudes a different kind of cool. Nicole looks effortlessly cute in everything from edgy rocker leather to shimmering backless gowns.
The famous socialite traveled to Miami for Art Basel in 2014, where she flaunted a lot of leg in an Emanuel Ungaro thigh-high split dress at a gallery opening. Her look de resistance is the effortless slip dress. The piece was inspired by a gilded Marc Jacobs gown at the CFDA Awards and a sheer floral Dolce & Gabbana number for the Wallis Annenberg Center for Performing Arts launch. Nicole recently joined Sofia Carson, Ariana Grande, and Doja Cat on the red carpet for the 2020 MTV Video Music Awards in New York City last August 30, having wowed audiences yet again for her exquisite taste in fashion.
Nicole Kidman
Nicole Kidman has been serving unforgettable red carpet looks since she stepped out in an iconic chartreuse chinoiserie John Galliano for Dior gown at the 1997 Oscars, putting her on a degree of best-dressed lists.
The Oscar-winning Australian actress has never been afraid to take a sartorial gamble, whether it’s in a red Balenciaga gown with a big bow or a shimmering Gucci gown with feathered parrots. Kidman is seriously on the pulse when it comes to dressing, nailing everything from street style to red carpet gowns (and pantsuits!). Nicole turned heads at the Big Little Lies season two premiere in NYC in her punked-up version of a black pantsuit. Her feathered-sleeved black Michael Kors Collection Fall 2019 sequin blazer was the perfect contrast to her chic tailored trousers. On another note, she wore an elegant strapless black gown by Armani Prive with a velvet bodice and an embroidered mesh skirt to the 2020 Critics’ Choice Awards.
Mila Kunis
Mila Kunis rose to fame on her credit role for the sitcoms That ’70s Show and Family Guy. However, it was her appearance in 2010’s Black Swan co-starring with Oscar winner Natalie Portman, as well as her alleged relationship with Ashton Kutcher, that catapulted her to the Alexander McQueen-wearing star we know today. Her rising celebrity status necessitated a significant wardrobe change. Kunis ditched her naturally curly locks for blowouts and shifted her red carpet wardrobe from jeans and tees to Lanvin, Fendi, and Phillip Lim gowns.
Some people might not know this because it’s a far cry from her more serious roles, but Kunis was voicing Meg Griffin on Family Guy in 1999. For her work on the animated program, it was natural that she graced award shows at the time. She was the envy of every teenage girl with this quintessentially 1990s look at the First Annual Teen Choice Awards. While we’re sure a tattoo necklace and butterfly clips were hard to resist, the star kept her accessories to a minimum. Fast forward to today, and the Ukrainian-American celebrity has found a stronger fashion sense. In a black dress and black heels, the actress looked sleek and smiley at the Los Angeles premiere of A Bad Mom’s Christmas at Regency Village Theatre on October 30, 2017, in Westwood, California.
Michelle Pfeiffer
Michelle Pfeiffer is one of the few people in Hollywood who proves that age is just a number. The Golden Globe winner and Oscar nominee has been gracing the red carpet for more than a decade, consistently impressing us with her glam ensembles, thanks to her bold and sophisticated sense of style.
Pfeiffer is one to be watched on-screen and off, from her tailored revival in the 1990s at the Emmys to her dazzling sartorial renaissance in 2018 at world premieres. She shows time and time again that you don’t have to be a certain age to wear a particular style or look. In a silver column gown, the actress had a princess-worthy moment on the red carpet at the Emmy Awards in 1999. Pfeiffer also appeared with Angelina Jolie at the Rome premiere of their new film, Maleficent: Mistress of Evil. This was held at the Auditorium Della Conciliazione in Italy last 2019. To her credit, the celebrity’s youthful glow and exquisite fashion sense prove to be timeless.
Meryl Streep
It’s safe to say you’ve got the red carpet game nailed down when you’ve been nominated for an Academy Award a record-breaking 21 times. Legendary actress Meryl Streep has bagged three Academy Awards and eight Golden Globes to her credit. She has been seen leaping through the streets of New York in casual wear and turning heads on red carpets in glamorous gowns off-screen as well. For Meryl Streep, who has been a nominee, winner, and host at the Oscars— as well as the Golden Globes, Emmys, BAFTAs, and SAG Awards—numerous times, picking a look to wear to the glamorous events is a piece of cake.
Meryl has retained a simple yet elegant aesthetic in Donna Karan, Valentino, and Lanvin designs during her four decades of attending award shows and other A-list activities. Off-the-shoulder skirts, wrap dresses, and fit-and-flare silhouettes are among her go-to styles. She dresses down in pantsuits, shirt dresses, or top-and-trouser ensembles for more casual occasions. Meryl’s design choices are perfect and on target, never OTT but still elegant and classy.
Lisa Bonet
Lisa Bonet fascinated men and women alike with her salt-of-the-earth beauty when she first stormed living rooms everywhere as the free-spirited Denise Huxtable, whipping through a dizzying lineup of bohemian getups.
Bonet emphasized her natural texture in the 1980s, with coiled bangs and a halo of voluminous ringlets framing her enviably prominent bone structure. She was a pioneer of the no-makeup make-up look, with a mostly bare face and brows swept up to feral effect, rather than defaulting to the de facto vibrant make-up of the time. Bonet and husband, Jason Mamoa, recently walked the 2020 Golden Globes red carpet and looked stunning in matching green ensembles. Momoa wore a velvet Tom Ford coat with Valentino trousers, while Bonet wore a couture Fendi gown. Not to mention his Cartier pin and watch. Mamoa’s stylist revealed the latter cost a total investment of $260,000 on his Instagram story.
Katy Perry
Katy Perry is one of the few celebrities who enjoy dressing up for a specific occasion. The artist, who has attended the Met Gala seven times, has regularly adopted the dress code with fashion-forward zeal. Take the year when she walked the “Heavenly Bodies” ball’s red carpet in a pair of larger-than-life angel wings.
Perry has made other credited appearances, though this otherworldly Versace production was by far her most fireworks-worthy moment to date. She leaned into the avant-garde aesthetic of the night with a custom Maison Margiela gown and full embroidered veil modeled by John Galliano for the Rei Kawakubo/Comme des Garçons show in 2017. On top of that, the Teenage Dream singer accessorized her custom Prada dress with a cheeky tech accessory: a ’90s-style Tamagotchi a year earlier for “Manus x Machina: Fashion in an Age of Technology.” Perry is bound to pull off an impressive red carpet look with a slew of kooky fashion moments under her belt—both on the Met steps and on stage.
Katherine Heigl
In a single word, how would you describe Katherine Heigl’s red-carpet style? It’s timeless. The actress from State of Affairs is a seasoned red carpet pro, as shown by her classic looks.
One of her iconic looks was a silver sequined dress by Bill Blass, as she poses in front of 27 models dressed for her film credit 27 Dresses. At the premiere of One for the Money in 2012, the Emmy Award-winning actress dazzled in a fiery one-shoulder Hervé L. Leroux style, breaking up her usual color palette. And wow, did she look amazing! Katherine won another red carpet award in 2012 while in Paris, wearing a goddess-like Maria Lucia Hohan silk mousseline gown. Katherine’s black strapless Escada mermaid gown from the 2007 Golden Globes topped the list, showcasing her always exquisite taste. Katherine Heigl returned to the red carpet for the LA premiere of her film Unforgettable in April. The actress wore a simple Blumarine gown with a slim-fitting silhouette that adds a powerful dose of sexiness.
Kate Winslet
Whatever happens on the Oscars red carpet, Kate Winslet will always channel old-school elegance with the kind of classic lines that conjure Grace Kelly’s glamour. The British actress has dabbled in unusual colors over the years and earned several awards, but she has always been careful to stick to the kind of classic silhouettes that would have pleased Old Hollywood’s costume-design madame Edith Head.
A garland of silk flowers draped over one shoulder complemented the classic gown. Winslet went big for her Titanic credit nomination, promising to wear Givenchy on the condition that the French couture house does not make a dress for any other candidate. Alexander McQueen modeled a deep-sea-green gown with gold silk thread and crystal embroidery in dragonfly and weeping-willow designs. Winslet made best-dressed news around the world with a custom design by London-based designer Ben de Lisi, who crafted a chic scarlet column dress for the actress for her third nomination.
Kaley Cuoco
The sitcom 8 Simple Rules gave Kaley Cuoco her first major credit role. She then landed a lead role on The Big Bang Theory two years later, and the show ended in 2019 after 12 seasons. Now, as the star of both DC’s Harley Quinn animated series and HBO Max’s The Flight Attendant, she’s set to take over streaming platforms.
The 35-year-old actress has since gained experience on red carpets and in the world of high fashion, but that doesn’t mean she hasn’t had her share of setbacks. Cuoco has been regularly well-dressed for award shows, movie premieres, and other activities in recent years, but no one was immune to the early 2000s style, including herself. The blonde actress began 2004 by attending the People’s Choice Awards in a light pink gown. She dressed to impress for her first big red carpet appearance. At the 2021 SAG Awards, Kaley Cuoco wore Prabal Gurung. It was quickly one of the favorites on the night, thanks to its voluminous puff sleeves, bold pink shade, dramatic silhouette, and decorative rosette. Her ensemble was completed by Messika jewelry.
Julia Roberts
Julia Roberts is an Oscar-winning actress who has appeared in hundreds of films over the course of three decades, and she has also established herself as a fashion icon. There’s no denying that the Pretty Woman star has worn some unforgettable looks during her career, whether it’s a jewel-encrusted ensemble, a chic pantsuit with heels, or a glamorous gown.
Roberts was a fan of long, boxy jackets in the early 1990s, which allowed her to show off her legs. In 1991, she accepted the Golden Globe for Best Actress in a Musical or Comedy for her film credit in Pretty Woman. America’s sweetheart was clad in this pinstriped miniskirt-suit, which was one of her most iconic looks. For the 2019 Veuve Clicquot Polo Classic in Los Angeles, the actress wore a bright navy and white two-piece ensemble with a white belt and matching Oxford shoes. With oversized sunglasses and tousled blonde waves, she completed the look.
Jessica Biel
Jessica Biel’s style has changed dramatically since her days on 7th Heaven as tomboy Mary Camden. The glamorous actress is now married to Justin Timberlake, with whom she has a son named Silas and has a successful Hollywood career. She’s also a sartorial force to be reckoned with, with designers lining up to dress her.
When the 37-year-old actress was cast in 7th Heaven, which debuted in 1996, she was just 14 years old. She’s been well-known for her appearances in films such as The Texas Chainsaw Massacre and The A-Team since then. Her most recent credit role as the lead in The Sinner earned her a number of nominations. The actress wore a beautiful white dress with half-circle designs to the 2018 Emmys, where she was nominated for The Sinner. Jessica Biel was back on the red carpet last February in California, promoting the third season of her show at The London West Hollywood.
Jennifer Lopez
Jennifer Lopez is one of the most well-known red-carpet celebrities. The dancer, actress, singer, businesswoman, and all-around entertainment power has mastered the art of making an entrance after being catapulted into the limelight in the mid-’90s with the star credits in Money Train and Selena. She never disappoints in looks by major labels, working with stylists including Andrea Lieberman and, most recently, Rob Zangardi and Mariel Haenn. From Versace and Gucci to Valentino and Zuhair Murad, Lopez attracts attention, makes headlines, and radiates her signature glow.
Lopez wore a black Georges Hobeika gown to the 2020 SAG Awards, which she accessorized with a casual $9 million worth of Harry Winston jewels. Jennifer Lopez’s sheer tropical-print Versace gown was perhaps one of the most memorable Grammys looks of all time. She went on to recreate the look for the designer’s Spring 2020 runway show.
Jennifer Lawrence
Jennifer Lawrence’s career has taken off since her first red carpet appearance in 2008. Her fashion sense has changed to a huge degree as her reputation has increased. The Hunger Games star gravitated toward one-shoulder looks and simple silhouettes during her early public event appearances. Now that she’s more secure in her own skin, the actress plays around with mesh specifics and bold designs. Lawrence has recently been seen at Hollywood events in a number of eye-catching outfits that perfectly illustrate her ever-evolving sense of style.
The blonde beauty kept things simple in a scarlet Calvin Klein Collection gown at her first Oscars ceremony in 2011. However, the fresh-faced starlet made headlines two years later by conquering the Golden Globes and Academy Awards in princess-style dresses from Christian Dior Couture. Lawrence has added metallics (a gold Prabal Gurung gown), Angelina Jolie–Esque slits (in Mugler), and a touch of the gothic saloon to her debut looks since then (in a macabre, ruffled Ralph Lauren Collection dress).
Jennifer Garner
Jennifer Garner is known for her glamorous red carpet looks, and her style has evolved to a significant degree since she first rose to prominence in Hollywood. During her early acting days, the actress wore trendy pantsuits and casual ensembles, but she has since gone on to walk the red carpet in Versace and Oscar de la Renta gowns.
In February 2000, she walked the red carpet with Scott Foley for the Los Angeles premiere of Scream 3. Garner wore a black pantsuit with black shoes and a shorter shoulder-length hairstyle. In March 2000, she began to drive her style in a new direction for the TV Guide Awards. She was dressed in a bright red gown with a matching shawl thrown over her shoulders. In 2019, she attended the Art of Elysium’s 12th Annual Celebration in a dress with a sparkly bow. She was dressed in a Gucci black sleeveless dress with a shimmering blue bow at the waist.
Jennifer Aniston
Jennifer Aniston rose to fame in the 1990s credits to a small-screen comedy named Friends and has kept her title as “America’s Sweetheart” ever since. Jennifer Aniston also looks as stunning as Rachel Green from Friends over two decades ago, thanks in part to her timeless sense of style. Her style has always been elegant, chic, and a little sexy at times.
At the 5th Annual Screen Actors Guild Awards in 1999, Aniston posed with her Friends co-stars, who were all dressed in matching hues. In a tiny crop top and jeans, Aniston was the only one who dared to expose more skin. Aniston stunned in a slinky, provocative black cutout gown at the SAG Awards in 2003, causing jaws to drop. In 2011, she stunned fans by attending her fragrance launch party in a cleavage-baring orange Vivienne Westwood minidress. Now fast forward to today, and Aniston is still slaying the red carpet. On January 19, 2020, she attended the 26th annual SAG Awards in a silk antique Dior gown.
Janet Jackson
Janet Jackson’s legacy has lived on in fashion almost as much as it has in her pioneering sound, from her early days as a child actress to her peak as one of the best-selling recording artists in pop music in the 1980s and 1990s. Being such a well-known pop-culture figure necessitates pushing a degree of boundary in fashion, which Jackson has done by wearing an often lavish wardrobe of looks over the years.
Jackson wore a black wool suit with a silver brooch and leather gloves to the 14th Annual American Music Awards in 1987. Jackson received her own star on the Hollywood Walk of Fame in 1990 when dressed in her famous Rhythm Nation costume from 1989. Jackson wore a black-caped gown with feathers and long evening gloves as he was inducted into the Rock and Roll Hall of Fame in 2019. Jackson wore a black leather utility trench coat with a matching leather headband to the 2020 Pre-Grammy Gala.
Jada Pinkett-Smith
Since her style motto is “try something,” Jada Pinkett Smith is one of Hollywood’s leading style icons. Pinkett Smith has experimented with just about every aesthetic imaginable during her time in the public eye over the last two decades. She wears a Versace sinful gown one night, a retro Lanvin ballgown the next, and by the end of the week, she’s sporting a studded leather jacket with fur cuffs. Pinkett Smith is a style icon since she credits emerging trends and encourages herself to experiment with her wardrobe.
Jada Pinkett Smith and her then-boyfriend, Will Smith, attended the premiere of Devil in a Blue Dress in 1995. She was dressed appropriately, literally in a blue dress! It was a two-piece knit dress with a maxi skirt and a bra top that is wrapped around her waist. Her back was also slung with a matching blue knit knapsack. When she arrived at the 2019 Grammy Awards in a bodysuit-turned-feather-gown, Pinkett Smith shot to the top of every best-dressed list. Roberto Cavalli Couture designed the pink dress, which was a perfect blend of couture, flapper style, and “Vegas showgirl.”
Isla Fisher
Have you seen Now You See Me? If you have, then you probably know who Henley Reeves is! The credit for the beloved role goes to none other than Isla Fisher, who also appeared in The Great Gatsby.
The star started her career in 1993. That would mean Fisher has been active for more than two decades. In the span of her career, the actress has accumulated a myriad of roles and recognitions. With her talent and undeniable charisma, this should come as no surprise. Due to this, the star is often on the red carpet. Throughout the years, she has stunned us with her red carpet looks. She always comes completely different from her last appearance. Do you know what has not changed? Fisher and her looks have always held this indescribable flair and unquestionable elegance and sophistication.
Halle Berry
Halle Maria Berry was born on 1966 in Cleveland. Many know her as simply Halle Berry— one of the prominent actresses in Hollywood. What some may not know is that she was also a beauty queen! Berry ranked as the runner-up in the Miss USA pageant. Later on, she placed sixth in the Miss World in 1986.
She has been in some of the biggest hits like X-Men, where she has the credit of playing Storm. The actress was also in Kingsman: The Golden Circle and John Wick: Chapter 3 – Parabellum. It would come as no surprise that because of this, she is often on the red carpet. The talented star has sported some of the most gorgeous red carpet looks. Usually, she is in shades of blacks and red, but recently, she has also tried on hues of pinks and purples. All in all, she has remained glamorous.
Drew Barrymore
Drew Barrymore has been walking the red carpet ever since she was a young child star. Now that the actress is 46 years old, she has displayed a significant style and looks evolution. From being grunge, her fashion is now all about glamour and class.
Drew started strutting the flooring of some of the most prestigious award shows in the ’80s, wearing cute and colorful dresses for kids, completing her look with a bow in her hair. She then began experimenting with her style in her teens with the signature trend of the ’90s—the thin brows and the white skin makeup. Come the early 2000s, Drew started investing in the most stylish wardrobe, making her appear every inch glam in silhouettes and striking color outfits. If there’s one thing that she has managed to maintain in her every look from then to today, it’s her perfect wavy hair.
Britney Spears
Britney Spears’ red-carpet style evolution can be perfectly described as from cute to daring. The Princess of Pop is fond of experimenting with her style when it comes to her red carpet looks. She goes from denim dresses to the most glamorous gowns that you can see. Would you believe her first red carpet outfit was a cute simple pink dress in 1999? She’s only 17 then, and her style fitted her age.
Everything changed when the millennium began, and Britney started to look fierce. Her appearance began to be the talk of the town, especially her crystal-encrusted bodysuit at the 2000 MTV Video Music Awards, which turned out to be one of her most famous outfits. The hitmaker, however, also has her fair share of infamous ensembles. Remember when she donned an all-denim dress alongside her then-boyfriend, Justin Timberlake, who also wore a matching denim suit? It became notorious to some degree for looking a little eccentric.
Gal Gadot
Gal Gadot has successfully made sophisticated-yet-sexy her trademark look on the red carpet. The former Miss Israel continuously receives credit for her stunning style whenever she will grace a special event. Her red carpet beauty is always coupled with her best fashion sense that always makes her appear incredible. The 35-year-old star’s fashion choices always nail the event she’s attending, like when she dripped in diamonds at the Oscars. She’s also not afraid to wear a tuxedo at one movie premiere.
Gal proves she’s not only brave in the movies, but she’s also bold in every way. She consistently shines on the red carpet—not just her shimmering dresses but her beauty as well. One of her best looks was when she wore a sparkling scarlet Givenchy gown at the LA premiere of her hit movie Wonder Woman in 2017, coupled with her captivating beauty. Gal proved she’s the perfect start to do the film, also thanks to her glam team.
Christina Aguilera
Christina Aguilera started to gain everyone’s attention after the release of her mega-hit song Reflection in 1998. Since then, the singer-songwriter began to dominate the pop music scene. Christina used to wear bare midriffs and leather chops at different music awards as a young pop star.
Now, The Voice judge has joined in the red carpet fashion of today, which is always a combination of elegance and sexy. Christina, of course, has every right to follow the trend. Gone are the days that Christina will opt for funky looks. She’s now the symbol of grace and beauty, walking the red carpet by wearing the most luxurious mega brands, like the likes of Roberto Cavalli and more. Christina won’t have any problem using her credit card to buy the most lavish outfits she wants, though. With a huge net worth in tow, she can pull off any look she wants.
Gwyneth Paltrow
Gwyneth Paltrow has been blessing fans with her glamorous red carpet beauty for the past 25 years. The 48-year-old star is mainly known today for her brave investments as an entrepreneur, but it can’t be denied that she always makes everyone stunned by her red carpet attires. She’s an A-list star in her own right, and she knows there are a lot of eyes watching her when attending different important events.
Gwyneth wears the best dresses from the most celebrated designers in the industry, like Tom Ford. She proudly sported his Gucci collections in the ’90s, making it a pillar of her own style. The actress has managed to exude Old Hollywood glamour, paired with a fresh-faced beauty. Years have passed, Gwyneth is now wearing her own line, G. Label, and she still carries the elegance she has displayed since day one, and she will continuously do so in the coming years.
Cindy Crawford
Cindy Crawford still looks like the supermodel that she is despite retiring. She can wear any dress that she likes, and it will look good on her effortlessly, thanks to her perfect long brown hair and sexy physique. Years may have passed, and she’s now in her 50s, but Cindy remains the same. She still looks as glamorous as before, making her a fan-favorite, not to mention a photographer’s favorite subject.
Everyone has admired her incredible style, from the ’90s until today. She always displays a stunning appearance whether she walks on the runway, the streets, and most especially the red carpet, and she displays elegance every year to a certain degree. As her name is synonymous with fashion, you can always expect her to wear the best pieces, whatever brand it is. Cindy knows how to perfectly play with her fashion choices, from style to color to the mix and match.
Brad Pitt
The red carpet fashion evolution is not only for girls; it applies to the boys, too. Think of Brad Pitt. In his more than three decades in the business, he has graced a lot of red carpet events. From a young man who looked really cute in his trendy outfits, he has changed to a guy who seems a real dapper. Everyone will agree that Brad is every inch handsome, so when you paired it with the most lavish clothing, he will be the epitome of hotness, getting all the credits he deserves.
Brad has an excellent fashion sense. As one of the A-list stars of today, he has access to every high-end brand, giving him the chance to select the best pieces to wear. Throughout the years, Angelina Jolie’s ex has put everyone in awe not just of his good looks but of his style and fashion sense that only someone like Brad can do.
Gabrielle Union
Gabrielle Union has proven time and again that she’s an absolute stunner. She doesn’t only make fans fall in love with her beauty; her charm always radiates in her smile whenever she walks any red-carpet events. The 48-year-old star always brings the ’90s iconic vibe from her classic movies Bring It On and 10 Things I Hate About You everywhere she goes.
Gabrielle used to follow Britney Spares’ fashion sense, wearing midriffs. Fast forward to today, and just like everybody else, Dwayne Wade’s wife has evolved into carrying the classiest look. She has upped her game when it comes to fashion and style, making an investment in the clothes she’s wearing. She manages to embody sophistication with her designer cuts that flaunt her excellent figure. Even if Gabrielle is not on the red carpet, she still looks every way stunning, even with her no-makeup look and casual outfits as she spends an ordinary day with her family.
Courteney Cox
Courteney Cox’s style has dramatically changed from her younger days to today. Everybody knows her as Monica Geller in the hit sitcom Friends, but people start to see a different Courteney when she steps on the red carpet. The 56-year-old star is about comfort and style, following her own fashion choices.
Do you remember how she wears dark lipstick in the ’90s, taking the ’40 style return to the loop back then? She’s not afraid to play with her appearance, experimenting not just with her clothing but with her makeup as well and, not to mention, her hair color. Courteney didn’t mind getting wild to a certain degree when it comes to her looks. She styled her hair with crayon-bright highlights when she attended the 1997 MTV Movie Awards, personifying her then-character Gale Weathers from Scream. Today, Courteney looks more uncomplicated but classy. She still has worn her signature black eyeliner, though, and hair gorgeous black hair loose, but it always fits her well.
Blake Lively
Another brave star who’s not afraid to make bold fashion statements is Blake Lively. She has been gracing the red carpet events in style since 2005. She started wearing jeans and oranges gowns back then, but she began experimenting by donning plunging necklines and miniskirts. Now, she makes everyone fall on their seats with her showstopping dresses and pantsuits, which she can perfectly pull off.
Making friends with some of the biggest names in the fashion world, like Anna Wintour and Karl Lagerfeld, may have benefitted Blake. They, too, commend her incredible fashion choices. Did you know she has graced a number of big runway shows, too? Yes, she did, and she always wears the most expensive couture at the said events. We wonder if Blake is doing careful investment planning for this. The 33-year-old star always leaves a good impression, even to the simpler events where she wears chic designer labels.
Ellen Page
If you’re wondering why Ellen Page, now known as Elliot, has always been the boyish type, he finally reveals the answer to this lingering question. The 34-year-old star announced his gender change in a lengthy post on Instagram. He now named himself Elliot, revealing he’s a trans, and his pronouns were he and they. Elliot is thankful for the people who have supported him throughout his new journey.
He would often don a pair of jeans and long sleeves back then, topped with a shirt. He then upped his style when he became a full-fledged Hollywood star, thanks to the success of his hit movies, Juno, Inception, Hard Candy, and more. He also gets credit for the hit TV series The Umbrella Academy. Ellen can bring off any kind of clothing, but you might always see him in pantsuits nowadays, which he could flawlessly pull off.
Cameron Diaz
Cameron Diaz may have stepped back from the limelight, but she will always be everyone’s favorite star. She oozes an incredible charm every time she smiles, especially when she walks the red carpet. The now-48-year-old star has made a number of unforgettable red carpet appearances that she, alone, can do. From the babyface young star that has made you smile one way or another, she’s now the symbol of refined beauty.
Cameron became a household name after she did the 1998 hit comedy film, There’s Something About Mary. At the time, she taught every one of her trans-seasonal dressing. Now, though Cameron has officially said goodbye from Hollywood, she still walks the red carpet with her casual look and understated neutral clothes, showing a high degree of fashion choices, however simple. Cameron is now into a power suit that always looks incredible on her.
Demi Moore
Demi Moore has already shown a commendable fashion style ever since she joined Hollywood. She’s always on the trend, from wearing palazzo pants in the ’80s to the most lavish gowns today. The 58-year-old star knows how to walk the red carpet in the most tasteful way, just like when she did in 2010, wearing an elegant cocktail dress by Chanel Haute Couture.
You may say she’s not taking the risk for her play-safe dresses, but it can’t be denied that she’s the symbol of understated glamour. She constantly radiates a different degree of sophistication that only she can do, consistently hitting the home run with her stunning ensemble. She knows how to put everyone in awe. With her long dark locks and trademark makeup, Demi consistently looks ravishing in her red carpet style, and everyone can agree with that.
Beyoncé
Beyoncé is easily one of the biggest names in Hollywood. All of her contributions to both the music and film industry are very well given credits to. Of course, she’s been in the industry for a long time, starting off as a member of the girl group Destiny’s Child.
Queen Bey is a triple threat. She has talents in dancing, singing, and acting. She doesn’t just have skills, though— the diva is an award-winning performer in all fields. If there’s one thing that Beyonce is most famous for, it’s that there is nothing she can’t do. Her songwriting process is so powerful, and she is also such a smart lady in real life. Beyonce has always looked good in almost everything— from fitted dresses in red carpet events to bedazzled costumes for her stage performances. Well, she has one of the best bodies in the world, so it’s easy to find clothes that complement her figure. She is a fashion icon, and indeed, her red carpet style has changed so much from the very first day we saw her to now, but both are still not so different. Both her past and present sense of style still has one thing in common— its fierceness.
Ariana Grande
Ariana Grande is one of the best singers of today, credits to her whistling and belting abilities, and also to her authenticity in everything she does. Ariana started off as a Disney TV star, and then she proceeded to the huge music industry, and not only did she make it, she became a record-breaking award-winning artist.
In terms of her personal style, we’ve all come to know Ariana with her signature ponytail hair. She definitely is one of the top three most followed female celebrities on all social media platforms. Her success and fame are on the roof! She is not only a great musician, but she is also a good person. She constantly has charity works and donations. On top of all this, Ariana is a master when it comes to fashion. The pop singer certainly has a vintage look which celebrities from the past have, but she does it with her own twist. From being a sweet-looking girl with red hair to being the lady with bangs to now just, Ariana constantly surprises us on all red carpet events.
Anne Hathaway
Award-winning actress Anne Hathaway has probably one of the biggest transformations when it comes to fashion. She is also known for being one of the rare actresses who personally chooses her outfits in events. The star knows how to make good investments on classic pieces, too, just like pieces of jewelry, shows, and other accessories to put her outfit together.
Anne is a big fan of Rachel Zoe, a designer and style consultant who is also very famous in her field. Zoe usually provides the fitting schedules and choices for her clients, who are mostly celebrities. Then, she’d be the one to contact the designer houses of the celebrity’s choice. Anne’s style went from sweet to sexy, but that change didn’t take over after a while. Even though her fashion still has a bit of similarity and a bit of “Anne” in it, she never fails to elevate it. The actress is also fond of changing her hairstyle from time to time. In fact, Anne perfected the art of pixie hair after she had her long mane shaved off for her role in the musical film Les Miserable.
Anna Kendrick
Rising star and one of the most sought-after actresses of today, Anna Kendrick, gives credits to her stylists for allowing her to explore her sophisticated side. She said that her style evolution wasn’t completely on her own but with lots and lots of help from the people around her.
For a celebrity like Kendrick, who always presents awards on a variety of shows, she needs to have good couture. Sometimes people wonder if her style had changed from the day she started her acting career as a cast from Twilight to the day when she made it big on the music industry. With Kendrick’s very in-demand career, she is also slowly becoming bolder and bolder with her fashion statements. The actress is constantly featured in fashion magazines, and she wears designer brands and couture dresses to the red carpet. Everything looks good on her. In Kendrick’s case, it wasn’t so much a change from sweet to daring but more of a change from simple to superstar. Some shops are even generous enough to allow us to shop for all of the outfits Kendrick has ever worn.
Anna Farris
Anna Farris is always one of America’s favorite actresses, credits to her natural charm and positive aura. One of the things to love about Farris is that she is so versatile in everything she does. Even in movies, she can do comedy and romance, she can be serious in a film, and people won’t see her as her character Britney in the famous Scream films. Farris is a great comedian, and she has such a unique voice. In fact, she is known for her husky and mellow voice, almost like something out of a computer.
Farris’ fashion transformation became obvious since she started off her acting career in the 2000s when fashion was diverse and short-lived. It was completely overshadowed either by the fashion of today or the fashion before its time which is the 90’s. The platinum-blonde star loved her hippie days, and some people even claimed that the actress had plastic surgery. Thankfully, Farris can carry whatever look she has at the moment.
Amy Adams
Amy Adams is one of the actors who are usually present on all of the awards shows. Credits to her outstanding performances for always getting her nominated by major award-giving bodies! Adams started off her career in minor roles until she landed a major part in the Disney movie Enchanted. She was young, and she looked so sweet on and off the screen.
Her sweetness hasn’t changed a bit these days, but her fashion evolution has been mind-blowing! Her shoe and jewelry collection are also breathtaking. She has incredible taste, and this one of the reasons why she remains to be one of the most beloved celebrities today. The change in Adams’ fashion isn’t so obvious, maybe because she already handled herself with elegance, class, sophistication, and poise right from the very start. Adams isn’t just a best-dressed female celebrity in red carpet events; she is also a fashion icon in her regular days, grabbing lattes and being photographed by the paparazzi.
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