The Academy Awards ceremony is the event of the year and its red carpet is basically just a fashion show featuring the who’s who in the entertainment industry. So of course, the A-listers make sure to put a little extra effort into their outfits. If by chance they win an award or present one on stage, they know their outfits will leave a lasting memory.
Styles and fashion have changed a lot though and what a celebrity thought was hot back in the day might not be anymore. Here are photos of stars at their first and at their most recent Oscars. These celebrities have definitely come out of their cocoons and emerged as butterflies on the red carpet.
Julia Roberts has been a regular on the Hollywood scene for more than 30 years and a lot has changed in fashion since then. At the 62nd Academy Awards in 1990, she was channeling her inner 90s supermodel after being nominated for Best Actress for Pretty Woman.
By the 91st Academy Awards, Roberts ditched the muted brown tones and way-too-casual hair and makeup for something a little more glamorous and memorable.
Director Spike Lee made his first ever Oscars appearance at the 62nd Academy Awards. At the time, he was nominated for Best Original Screenplay for the film Do The Right Thing. He lost out on the Oscar but even as a young director Lee used his Oscars fashion to make a statement.
In 1990, he attended the awards with a Malcolm X pin on his suit. In 2019, he paid tribute to Prince with his purple ensemble and made a political speech during his award acceptance.
South African actress Charlize Theron has always been drop-dead gorgeous but it seems like she gets even more beautiful and more high-fashion as she grows older. Theron had been starring in movies for years but at the 72nd Oscars in 2000, she had starred in four films and been dubbed Hollywood’s new “it” girl.
Young and innocent in 2000, by the 91st Academy Awards, Theron was ready to risk it all in this covered up yet barely-there look.
Back in 1997 when J-Lo attended her very first Academy Awards, she was hot off the success of her first major motion picture, Selena. Lopez portrayed the late Latin American singer in a biopic and it put her on the woman to watch list for films.
More than two decades later and it looks like Jenny from the Block hasn’t aged a day. Lopez knows it too, which is why she chose to rock a body-hugging silver dress for the 91st Academy Awards.
Between the 72nd and 91st Academy Awards, Queen Latifah went from wearing your grandmother’s hand-me-down church dress to wearing a style fit for a real queen. She may have been only 30 years old at her first Oscar red carpet but she looks like she hasn’t aged a day since swapping out her grandma’s clothes.
She landed her first spot on the Oscars red carpet after starring in The Bone Collector opposite Denzel Washington and Angelina Jolie. Not too shabby.
Over the last few years, actor Chadwick Boseman has made a name for himself as a fashion force to be reckoned with. He’s now known for taking chances and wearing prints and patterns that pay tribute to his African American roots.
Before he had found his way in fashion, Boseman’s wardrobe was like most male wardrobes in Hollywood: tailored suits in different colors. If the last few years are any indicator, Boseman’s style is just going to keep getting better.
Actress Glenn Close is no red carpet rookie. She first walked the Oscars red carpet at the 56th Academy Awards way back in 1984. It wasn’t exactly hard to guess when that photo was from though since the black lace frock with puffy sleeves screams “eighties.”
More than 40 years later, Close has aged like fine wine and has opted for some more timeless pieces to walk the red carpet in. This gold gown with a cape can never go out of style.
Amy Adams is now known as the one to watch for Oscars fashion. Back in 2006? Not so much. At her first-ever Academy Awards red carpet, Adams must have thought a brown taffeta gown with accent stripes would be timeless.
We’re glad to see she hasn’t shied away from using patterns and texture but now she’s doing it in a much more timeless way. We’re sure this fashion icon would like to forget about the 2006 Oscars.
She may be known for her crazy outfits (who could ever for get the meat dress) but Lady Gaga has always known what to channel her inner glam monster. Gaga’s first Academy Awards attendance was in 2014 and it was immediately obvious she knows how to dress for the occasion.
Her fashion sense has just grown over the years and at the 91st Academy Awards, she went full-blown Hollywood glam as she rocked the 128.54 Tiffany Diamond around her neck.
Between the 80th and the 91st Academy Awards, Viggo Mortenson went from being a creepy vampire with a power stance to being a charming dad with a power fashion sense.
The main takeaway from Mortenson’s transformation is that a tailed suit can do you wonders. He was nominated for best actor in at both award shows. While we’re sure he would have loved to take home an Oscar at either show, he sure looked better at the second one.
J-Hud’s first Academy Award appearance was at the 79th award show when she took home the Oscar for Best Supporting Actress from her role in the film Dreamgirls. The film was Hudson’s first major project after competing on American Idol. By the looks of her red carpet dress back in 2007, she just wasn’t entirely confident being a style icon.
Fast-forward to the 91st Academy Awards and Hudson is oozing sexiness and confidence with her one-shoulder red dress.
Bradley Cooper gets a lot of press every year on the Oscars red carpet even though the man looks the exact same and always plays it safe. Aside from growing a beard, Cooper looks the exact same. Honestly, it’s a bit of a snoozefest.
The only major difference between the 82nd Oscars and the 91st is that in 2019, Cooper was attending as both an actor, a director, AND a performer.
On the completely opposite end of the spectrum, actor Chris Evans at least understands that if you’re going to look the exact same for more than a decade then you have to switch up your style.
Like Cooper, Evans also opted to grow a full beard between the 85th and 91st Oscars. He also decided to throw out the Men in Black suit and try something more daring, like a blue velvet jacket.
If there’s anything we’ve learned from seeing Paul Rudd on the Oscar red carpet in 1999 versus 2019 it’s that he doesn’t age. Seriously, he might be an immortal being. In fact, he’s actually giving off more of the vampire vibe than 2006 Viggo Mortenson was, and in a much less creepy way.
While he’s been busy drinking the elixir of life, Rudd has also found the time to get a haircut and hire and new tailor. It’s truly a miraculous transformation.
Regina King actually had a busier film career in the 1990s and early 2000s, but she didn’t garner an Academy Award nomination until 2019. For the event, she chose a classic white gown with the perfect amount of ruching and draping to show off her curves.
King must have known she was a shoe-in to win Best Supporting Actress because unlike her look at the 77th Oscars, this look is timeless.
Laura Dern first gained international attention in 1993 for Jurassic Park, but her first Oscars appearance was one year early at the 64th Academy Awards. At the time, she was nominated for Best Actress for her role in the film Rambling Rose.
Dern didn’t win the award but she left a timeless mark on the red carpet in her nude, lace gown and Marilyn Monroe inspired hair-do. Her 2019 look is equally beautiful, but we’d argue she looked more glam back in 1992.
Actress Brie Larson has been in and around Hollywood since she was a young teenager but she didn’t make it to the Oscars red carpet until 2016. At her first appearance, she was nominated (and won) the award for Best Actress for her role in Room.
While she looked fresh-faced and innocent back in 2016, at the 91st Oscars she played up her new character Captain Marvel. In an edgy silver dress and bleach blonde hair, Larson definitely looks like she could kick our butts.
The only celebrity who is more boring on the red carpet than Bradley Cooper is Christian Bale. I’m actually 99.99% sure he recycled his suit from the 2011 Academy Awards to attend the 2019 ones.
Bale’s style “transformation” (or lack thereof) is somewhat shocking, considering the fact that he is known for his drastic physical transformations from film to film. Maybe he decided to play it safe in 2019 because he had just dropped 40 pounds that he packed on for his role in Vice.
The queen of Wakanda hasn’t exactly been the queen of the Oscars red carpet. While we don’t have enough praise for Angel Bassett’s one shoulder pink dress that she wore for the 91st Academy Awards, we have a lot of questions about the outfit she wore to the 67th.
Bassett’s white lace top with a way-too low cut black dress over top looks like it’s from Mortica Addams closet. We’re glad she’s smarted up style-wise over the years.
She’s played the queen and she’s always looked like one too. Well, she definitely looked more like a queen at the 91st Academy awards versus the 67th. Mirren’s 1995 outfit was definitely thought to be chic and fashionable at the time but looks like it was better suited for a British garden party than the Oscars red carpet.
Over the years, Mirren has clearly learned to add some bling and find a timeless gown to rock on the red carpet.
Mahershala Ali might have only attended three Academy Awards but he’s made an impact at every single one. At the 2017 Oscars, Ali took home the award for Best Supporting Actor after playing a drug dealer in Moonlight. For his first Oscars, he played it safe with a classic suit.
Two years later, Ali won again but this time in a much more daring Oscar outfit. The patterned jacket, collarless shirt, and black beanie is definitely a memorable look.
Actress Octavia Spencer has always glistened in a glamorous gown on the Oscars red carpet. At her first appearance at the 84th Academy Awards, Spencer took home the Best Supporting Actress award in this stunning, white Grecian goddess-inspired gown.
At the 91st Academy Awards, Spencer wasn’t up for any individual awards but the film she executive producer, Greenbook, took home the award for Best Picture. That win alone is deserving of the beautiful sparkling blue ballgown.
Like Amy Adams, Emma Stone is another actress who often wears timeless gowns to the Oscars. The beautiful, bold red gown that Stone wore the the 84th Academy Awards set her on a path to red carpet dominance.
Over the years she’s kept up with classic silhouettes but at the 91st Academy Awards, she took a chance and stepped outside the box for this metallic, structured shoulder look. There’s no doubt that Stone is always on the forefront of red carpet fashion.
Pharrell Williams is now known for being a style icon and revolutionary. I mean, who can forget the massive hat? So it’s kind of shocking to see Williams play is so safe in a classic black tuxedo for his first Academy Awards red carpet.
Maybe he was just feeling the crowd at the time because since then he’s transformed and never been afraid to try new styles out. We’re not entirely sure about the camouflage shorts on the red carpet but we respect that he took a chance.
Rachel Weisz is that actress that women love to obsess over because she kind of feels like a Wiccan who has a hidden amulet under her gown somewhere. Women love hidden amulets. Weisz’ 2006 Oscars look is safe and in all honesty, a little bit boring.
BY 2019, the actress has clearly found away to maintain her mysterious charm while serving up some high fashion looks. Now, seriously Rachel, show us your powers.
Kelly Ripa has been a television personality for more than two decades but she didn’t garner an invite to the Academy Awards until 2013. The talk show host flew solo at the 85th Oscars in a bold A-line gown.
Ripa kept up her habit of bold prints for the 91st Oscars, but this time is a huge, flowing ballgown. For someone with such a petite figure, Ripa can really make it work.
Okay, we know that James McAvoy was almost 30 when he attended the 79th Academy Awards but he looked like a lost teenager that we just want to snatch up and show him the way. Since 2007, McAvoy has transformed into an incredible actor who takes on complex roles.
Unfortunately, his fashion has stayed just as safe and plain as always. He may have grown out of the long shaggy hair, but he’s still dressing like a kid at his bar mitzvah
Melissa McCarthy is one of the most underrated glam stars on the red carpet. The actress has been a huge supporter of body positivity and has always found looks like show off her curves in all the right ways.
At the 84th Oscars, McCarthy wore a gorgeous but relatively safe pale pink gown. Seven years later, she’s transformed into a fashion queen with enough confidence to rock pants and a cape.
Sarah Paulson might be one of the fashion transformations we’ve hated watching. At her first Oscars red carpet, Paulson was 100% glam in a nude, beaded gown that was simple and elegant.
At the 91st Academy Awards, we respect that she took a change with a pink two-piece ball gown but at what cost? Pink might have been the color of the night but it couldn’t save Paulson from looking like she’s wearing a bib to the most glamorous party of the year.
You’d think for being one of the top fashion designers in the world, Tommy Hilfiger would have known better back in 1999 not to wear a frilly blue shirt to the Oscars. Seriously, that blue shirt looks like it could have came straight out of Jerry Seinfeld’s pirate shirt closet.
Twenty years later, the fashion designer has finally discovered fashion on the red carpet. Not everyone can pull off a plaid suit jacket but Hilfiger sure can.