When on the red carpet, stars always want to look their best and avoid being placed on the Worst Dressed list. Many of the celebs in this article have learned how to perfect their look over the years, but their past fashion crimes are now here to haunt them.
Cher – Then
At the 1986 Academy Awards, all eyes were on Cher as she took the red carpet by storm in this eye-catching exquisite ensemble by Bob Mackie. To this day, the outfit and headpiece have gone down as one of the most iconic red carpet looks that no one else could ever pull off.
Cher – Now
Cher might be 71-years-old now, but her age-defying looks have continued to wow everyone on each red carpet she walks. At the 2015 Met Gala, Cher donned a Marc Jacobs embellished gown and walked the carpet with the designer himself. She left her long raven locks flowing and her make up in hues of red to match the stunning dress. The “Believe” singer may have sold over 100 million records worldwide, but there is now slowing her down as she continues to perform in her residency.
Jennifer Aniston – Then
Jennifer Aniston first gained recognition for her role as Rachel Green in Friends. Aniston quickly became America’s sweetheart with her stunning looks and outgoing personality. The starlet was seen walking the 1999 Academy Awards red carpet with her Friends co-stars in this daring two-piece Versace dress. Aniston teamed her look with a delicate necklace and her famous ‘The Rachel’ hairstyle. There are not many actresses who could have pulled off this look, but Jen made it look effortless and chic.
Jennifer Aniston – Now
Aniston has come a long way in her career and is considered one of the biggest A-list actresses in Hollywood today. At the 2015 Academy Awards, Aniston hit the red carpet in an asymmetrical, one-shoulder, champagne beaded gown by Versace. The slit in the side of the dress showed off just a glimpse of the actresses legs, all while keeping it classic. Jen left the jewelry to a minimum and let the stunning dress do the talking.
Kate Winslet – Then
In 1998, Kate Winslet took to the red carpet of the Golden Globes with Titanic co-star, Leonardo DiCaprio, by her side. Winslet was just starting out in her career and Titanic catapulted her to stardom, becoming one of the highest grossing movies of all time. Winslet wore a Ralph Lauren gown which clung to her every curve and paired it with a diamond choker and a bold red lip. Her fashion choices back in the 90s were polar opposites to today.
Kate Winslet – Now
In 2016, Winslet wowed at the Academy Awards in this black, shiny Ralph Lauren gown. Kate looked every inch the movie star as she gave her best poses on the red carpet, appreciated by paparazzi and adoring fans. The actress went for simplicity with her jewelry and hair, going for stunning diamonds and a loose beachy wave. Although many hailed the actresses outfit choice, opinion was split and many people said that they had seen her in better gowns.
Sarah Jessica Parker – Then
Sarah Jessica Parker is a major fashionista today, but before her Sex And The City days, she went for simple over sophisticated. At a 1997 premiere, Parker hit the red carpet in a simple, white slip dress, paired with matching white strappy heeled sandals. Sarah had a typical 90s up-do and light pink eyeshadow to finish off the look. We’re not sure if Carrie Bradshaw would approve of this one, but Sarah can pretty much pull off anything she wears.
Sarah Jessica Parker – Now
In 2014, Sarah Jessica Parker stunned on the Met Gala red carpet in this one of a kind, Oscar De La Renta dress. Usually designers do not put their names on their garments, but in this case, it was appropriate for the event which brings the highest of couture and only the A-list in celebrities and designers. Parkers look was completed with long white gloves to give it an old-fashioned classical look, and she ensured all eyes were on her.
Madonna – Then
Madonna was never an artist who played by the rules, so when she showed up to the 1984 MTV VMA red carpet in a lace wedding dress for the premiere of the hit single “Like a Virgin” no one could get enough of it. The infamous outfit with the “Boy Toy” belt went on to make history and has been replicated a number of different artists including Britney Spears and Christina Aguilera in later years. This was one of Madonna’s most memorable looks.
Madonna – Now
Despite being in music for over three decades, Madonna has not calmed down her fashion choices with age. At the 2017 Met Gala, Madonna wore custom Moschino and paid homage to the armed forces in this camo inspired gown. Madonna looked every inch the daring fashionista and never afraid to do something outrageous and break the rules. The gown was accompanied by a parachute bag, leather gloves, and a chain. Many hailed the singers choice to do something different.
Jane Fonda – Then
Jane Fonda was one of the biggest icons in the 80s with her workout videos taking the fitness world by storm. At the 1990 Academy Awards, Fonda exchanged her leotards and leg warmers to a stunning gown and arrived with her husband, communications mogul Ted Turner in this stunning electric blue dress. The beaded top half made Jane look every inch the celebrity and the fishtail train gave it that extra wow factor. She looked every inch an Oscar-winning actress.
Jane Fonda – Now
After taking a hiatus from acting, Jane went on to star in films including Monster-In-Law, Georgia Rule, The Butler, This Is Where I Leave You and Youth. Despite now being 80-years-old, Jane Fonda still looks incredible and most would never guess her age. At the 2015 Grammy Awards, Jane stunned in this emerald Balmain jumpsuit that most people half her age could not pull off. Fonda continues to kill it in the style stakes and is known for slaying every red carpet she walks.
Angelina Jolie – Then
Angelina Jolie got her start as a child star, getting her debut alongside her father, Jon Voight, in Lookin’ to Get Out. However, it wasn’t until a decade later that Jolie got her big break and began hitting the red carpets. In 1999, Jolie showed off her classic style in this simple, off the shoulder, white dress, paired with a diamond necklace and loose hair. Through the decades, Angelina’s style has truly evolved, but she has never failed in looking classically beautiful.
Angelina Jolie – Now
Fast forward to 2018 and Angelina showed off her effortless beauty on the Golden Globes red carpet. Dressed in a chic black Atelier Versace gown, adorned with a sheer top and feathered sleeves, Angelina stunned and showed the rest of Hollywood what pure glamour looked like. This was one of Jolie’s first major red carpets in years without estranged husband Brad Pitt, but the actress looked strong, bold and beautiful. Jolie is always one to watch on the red carpets.
Dolly Parton – Then
At first glance, you might not have a clue who this is, but if you think country music sensation, you will know that it is none other than Dolly Parton back in 1978. Parton’s style has truly evolved over the years, but she has never been one to shy away from experimenting with fashion. This green dress, covered in multicolored flowers was one of Dolly’s bold looks. She added a strong red lip and her iconic bouffant hair to tie it all in together.
Dolly Parton – Now
At 72-years-old, Dolly Parton is still at the top of her game in music and is one of the greatest icons country music has seen. Parton has sold over 100 million records worldwide and was the most honored female country performer of all time. Just because of her age, Dolly had no intention of toning down her outfits or conforming to what society expects of her. She turned up at the American Country Music Awards in this stunning champagne lace dress that hugged her curves.
Julia Roberts – Then
Considering what she looks like now, it is hard to believe that Julia Roberts turned up to the 1990 Golden Globes in this vintage oversized masculine suit. At just 23-years-old, Roberts was new to the industry and it was one of her first times at a major award show. Julia’s striking looks, fiery red hair and infectious smile led people to think that she was one to watch in the industry and her acting spoke for itself. This suit was a far cry from her role as Vivian!
Julia Roberts – Now
Nowadays, Julia Roberts is one of the biggest A-list stars in Hollywood and she regularly stuns on the red carpet. At the 2016 Cannes Film Festival premiere of Money Monster, Roberts looked absolutely gorgeous in this Armani Prive, structured black, off the shoulder gown, let her hair flow loose and completed the look with a diamond and emerald teardrop necklace. Roberts showed the awaiting paparazzi and fans what a true A-list star looks like and she was one of the best dressed on the night.
Gwen Stefani – Then
Gwen Stefani started out in rock band No Doubt and back in the 90’s, she played the part of the female rocker. Stefani had no qualms about hitting the red carpet in a bikini top which matched her blue hair, with an unusual skirt over pants and some platform sandals. Her outfit was very typical of the 90s and Gwen was seen as a trendsetter. To finish off her unique look, she had rhinestones placed around her eyes.
Gwen Stefani – Now
Stefani has come a long way since her days of having different colored hair. At the 2017 Vanity Fair Oscar Party, Stefani stunned in this sheer Reem Acra gown which just about covered her in all the necessary places. Gwen let the dress do the talking as the designer put some intricate flower detailing into it, along with a beautiful train. She completed her look with a matching red lip and a small clutch, not to mention her best accessory, boyfriend Blake Shelton.
Mariah Carey – Then
In the early 90s, Mariah Carey was a breakout star and she was becoming a regular feature on red carpets. At this time, Mariah was rocking her signature curls and baby face, but everyone was blown away by her incredible vocals. Carey donned this scarlet crossover dress at the 35th Grammy Awards, adding hanging diamond earrings and bracelet to her look along with a matching scarlet purse. Mariah was nominated for two awards at the event.
Mariah Carey – Now
Mariah quickly became an international superstar and she has sold over 100 million records to date. The starlet is a regular feature on red carpets today and at the 2018 Golden Globe Awards, she wowed in this Dolce and Gabbana number which accentuated her curves in all the right places. The simple black gown meant that Carey could accessorize with millions of dollars worth of diamonds, but she pulled it off perfectly because she is Mariah Carey and is known as a diva!
Britney Spears – Then
Back in the 90s, Britney Spears was a southern girl who was climbing up the ladder to become a singing sensation. She was adored by many and quickly became known as America’s sweetheart with her infectious smile and outgoing personality. Spears showed up to a red carpet wearing this baby pink slip dress, sandals and a headband, showing her innocence and teenage years. With her first hits including “Baby One More Time” and “Crazy,” Britney was well on her way to seeing international success.
Britney Spears – Now
Over 20 years later and a very public meltdown, Britney got back on the top of her game and looked better than ever. The pop princess attended the 2016 MTV Video Music Awards in this cut out Julian MacDonald number, showing off Britney’s amazing dancer torso and incredibly toned legs. She let her blonde locks flow loose and flashed a smile to the waiting photographers. Having sold over 100 million records in her career and becoming an icon, it is no surprise that Britney looks better than ever.
Brooke Shields – Then
Actress Brooke Shield got her start in movies from a very young age, going from a child model to child actress. In the early 90s, Brooke returned to the big screen after taking time out of her career to attend college. She attended the 1998 Golden Globe Awards looking every inch the movie star. Shields was a vision in red with this scarlet strapless gown and matching pashmina. She exuded glamour with her luscious red lips and old Hollywood hairstyle.
Brooke Shields – Now
Brooke Shields is one of those actresses who has defied their age and looked incredible throughout the years. Brooke attended the CFDA Fashion Awards in 2017 in this gorgeous Sachin and Babi gown, complete with black satin pants shown through the central slit of the dress. The floral dress was finished off with an impressive train and Shields ensured that all eyes were on her outfit as she went for a simple look with minimal jewelry and simple makeup.
Sandra Bullock – Then
Sandra Bullock was one of the biggest rising stars in the 90s. She had a string of hit films including Speed, While You Were Sleeping, The Net , A Time to Kill, Hope Floats, and Practical Magic. Sandra attended the Golden Globe Awards in this unique purple, embellished dress, with a matching purse to accessorize. Sandra’s hair was in a loose up do, and was very typical of the 90s style. The smile on her face might suggest all the success she had had that year.
Sandra Bullock – Now
Not only was Bullock named one of the most beautiful women in the world, she was also one of the highest paid actresses and an Academy Award winner. At the 2018 Oscars, she wore this stunning Louis Vuitton gown which was made to perfection. The beadwork on the dress was exquisite and went from black to gold in an ombré look. Sandra left her hair simple and sleek and allowed all of the attention to be on this couture gown.
Olivia Newton John – Then
Olivia Newton John wasn’t just the much loved Sandy from Grease, she was also an 80s fitness icon and her huge success saw her release a number of singles and albums. At the 1983 Grammys, Olivia turned heads in this fuchsia, frilled, off the shoulder gown, complete with a matching choker. Olivia went for the 80s mullet to bring her look together, but although it wasn’t one of her best, it was certainly very on trend at the time.
Olivia Newton John – Now
Olivia Newton John doesn’t attend nearly as many red carpets as she used to in the 80s and 90s, and is more regularly seen on tour in her native Australia. However, in a rare appearance, she attended the 2016 Country Music Awards, shunning a dress and going for an androgynous pantsuit, complete with leather trousers and a jacket with turquoise detailing. The 69-year-old certainly has age-defying looks, but she has no intention of slowing down.
Renee Zellweger – Then
Renee Zellweger got her start by appearing in Texas Chainsaw Massacre: The Next Generation and the critically acclaimed Empire Records. The actress was seen on many red carpets throughout the 90s and went for a more simplistic, classic style. Here, she was dressed in a pale green slip dress, complete with a dark lip and loose, flowing locks. Renee looked every part the girl next door and went on to become everyone’s favorite British girl, Bridget Jones.
Renee Zellweger – Now
Renee Zellweger seemed to have dropped off the radar in terms of acting and appearances in recent years, but in 2017, she made an appearance at a movie premiere in this canary yellow Carolina Herrera dress. The vibrant dress worked seamlessly with her skin tone and the corset top provided the actress with some great shape and structure. She added a pair of ivory snakeskin pumps to bring the look together. Zellweger looked a far cry from her Bridget Jones’ days.
Rachel Weisz – Then
Rachel Weisz made her film debut in 1994’s Death Machine. That same year, she also had some luck in the theatre, appearing in the London engagement of Noel Coward’s Design for Living. Though her style at the time was quite understated, no one could fault her for choosing a classic black dress to wear to her very first red carpet. Since her early days of minimalism, both Weisz’s sense of style and on screen skills have continued to blossom.
Rachel Weisz – Now
Rachel Weisz has become one of the most well regarded actresses of our time, and her fashion choices have certainly kept up with her work. Even at 48 years old, the actress has still retained a youthful look, though her choice of gowns is certainly more daring than they were 20 years ago. Here Weisz is dressed in a whimsical blue patterned with flowers made even more sophisticated by a row of silver buttons that mirror the slit baring her leg.
Sofia Vergara – Then
Sofia Vergara made the transition from Mexican TV to Hollywood in the early 2000s. Plucked from the beach of her native Colombia, Vergara’s looks were always stunning, but as she began moving from modeling into acting, it became clear just how much talent she would hold. Sofia took a daring risk on this lace and sequin ensemble that bared her midriff when she made this red carpet appearance at the American Comedy Awards in 2000, one of her first appearances in America.
Sofia Vergara – Now
Vergara’s ethereal beauty hasn’t seemed to wane in the intervening years, as she’s only become even more gorgeous with age. Her style has certainly evolved as she’s risen through the ranks of American television to become the highest paid actress on TV today. Vergara wore this incredible dress to the 2018 Oscars, a far more chic play on her red carpet look from yesteryear. With a cascade of crystals running down a cape, Vergara looks every inch of the TV queen that she is.
Claire Danes – Then
Claire Danes was primed to become a star from her youth, having two artists for parents while growing up in the hip Soho neighborhood of Manhattan. It wouldn’t take long before her performing arts school education paid off, as Danes quickly went pro when she was barely even a teen. At 15, she won her first major role with the lead character in My So-Called Life, which lead her to this red carpet moment. Every inch of her dress screams classic 90s.
Claire Danes – Now
Claire Danes has since become a bonafide movie star, appearing elegantly at every industry event required. However, even the best of us have a mishap now and again. Danes outfit at the 2017 Met Gala was widely derided, particularly for the overly showy shirt that gave the illusion of having just gotten off of a pirate ship. Since then, Danes seems to have returned to a more classic style of gown for other red carpets she has attended.
Demi Moore – Then
Demi Moore was always considered one of the most beautiful actresses. In 1989, she showed up to the Academy Awards in a bizarre outfit which she was said to have designed herself. The long sleeved corset paired with a half skirt and bicycle shorts was something that no one expected from the actress and she definitely raised a few eyebrows on this one. Demi added a diamond and gold necklace and earrings to accessorize, along with a pair of black and gold pumps to bring it together.
Demi Moore – Now
Nowadays, Demi Moore’s style has completely evolved from that in the 80s. At 55-years-old, people were in awe of Demi’s youthful looks and physique and asking the actress her secrets to looking so perfect. At the Screen Actors Guild awards in 2016, Demi made everyone envious of her figure in this semi-sheer Zac Posen number, which showed off her assets beautifully. Moore kept the makeup simple and elegant and added some diamond bracelets and earrings for some sparkle.
Gwyneth Paltrow – Then
Gwyneth Paltrow was another rising star in the 90s and she gained worldwide recognition for her role in Shakespeare in Love, which led her to win the Academy Award and the Golden Globe Award for Best Actress. At the Golden Globes, the actress wore this simple yet elegant pink flowing dress, staying age appropriate and classic. Paltrow left her hair loose and went for just a touch of makeup to highlight her facial features, and a silver purse to finish the look.
Gwyneth Paltrow – Now
Gwyneth Paltrow has always seemed to get her outfit choices right and usually ends up on the best-dressed lists from high profile events. At the 2017 Met Gala, Paltrow stunned in this fuchsia gown by Calvin Klein, complete with sheer panels, long sleeves, and an impressive trail which ran down the steps of the iconic Metropolitan Museum of Art. Paltrow kept her hair simple and tied back, although many had hoped she tidied it up a little more.
Courtney Cox – Then
Courtney Cox got her big break as Monica Geller in hugely successful sitcom Friends, and almost immediately, the cast were being nominated for awards including Primetime Emmys. At the 1995 Emmy awards, Courtney donned this lilac, silk halter neck dress complete with a plunging neckline and thigh-high slit. She added a matching choker and pair of lace-up pumps to complete the look. Cox’s hairstyle was synonymous with Monica for many seasons on the much-loved sitcom.
Courtney Cox – Now
Courtney Cox saw huge success in her career and she became a regular on a number of high profile red carpets. At the 2015 Grammy awards, Cox wore this gorgeous babydoll embellished dress by Marc Jacobs, complete with a sparkling bow neckline and a pair of simple black sandals. Courtney left her hair loose and wavy, ensuring that her look was not too over the top. It was the perfect outfit for the Grammy awards and Courtney’s look was hailed by many.
Janet Jackson – Then
Janet Jackson was the cool sister in the Jackson family and was never afraid to break the rules in the music and style stakes. Janet attended the 1994 MTV Video Music Awards in a super casual overall, black sweater, baseball cap and combat boots. Jackson’s beautiful smile was infectious and her whole look seemed to work, purely based on her personality. Jackson was known for her provocative performances and outfits on stage, so this was relatively normal for the singer.
Janet Jackson – Now
Janet Jackson has had many ups and downs in her life which led her to shy away from the spotlight at different stages. In 2017, she made a rare appearance at a red carpet event, dressed in this unusual outfit by David Ferreira. The fur waist coast, paired with leather leggings, a trailing skirt and gloves would look absurd on anyone else, but Janet just pulls it off like it is normal. Her slicked-back hair, tied into a braid makes it look chic yet cool.