Taylor Swift - 2008
In 2008, Talor Swift was still at the beginning of her career. She was a budding country music star that tweens were obsessing over, and everyone was jealous because she started dating Joe Jonas. Things were going well for Swift, but her style was a bit on the dull side.
Swift would often wear her hair down with her natural curls, and most of her red carpet looks were things you could find off the rack. When she first started going to red carpet events, she opted for princess-style looks or dresses with cowboy boots.
Taylor Swift - 2019
When Swift attended the 2019 Billboard Music Awards at MGM in Las Vegas, she wore this stunning, structured lavender gown. It looks like she finally found a more sophisticated style that shows off her best assets.
Every time Swift has released a new album, she had switched up her style, and it is incredible how much she had changed. She is almost unrecognizable from her country music days as a bright-eyed teen.
Kim Kardashian - 2009
It took a while for Kim Kardashian to become a style icon. When we think back on the early days ofKeeping Up with the Kardashians, her outfits were almost comical, and she probably wouldn't be caught dead in most of them today.
We have to thank Kanye West for upping her style game. When they met, he basically gave her a makeover and made her into the style icon we know and love. Take this bubble skirt, for example; she wouldn't even think to try on this outfit now.
Kim Kardashian - 2018
Flashforward to the 2018 Met Gala, where Kardashian wore this stunning gold number that made people gasp because it was so fabulous. She looked like a golden goddess and was one of the top looks from the night.
Kardashian is not afraid to show off her body, but she is also much more open to athleisure looks these days. How else would she comfortable study for the BAR exam unless she was wearing Skims sweats?
Lizzo - 2017
Ever since Lizzo came onto the scene, she has always been a voice for body positivity and wearing whatever you want. Although we loved the message, her style was a bit bizarre back a few years ago.
At the 2017 MTV VMAs, Lizzo dressed as a funky bride in a white floor-length gown with a sweeping skirt that had the title of her debut song in bright letters. She paired it with tights and bedazzled sneakers, but this look didn't get her on the best-dressed list.
Lizzo - 2020
While Lizzo still wears funky outfits, they are much more refined. For the 2020 Grammys, she wore this stunning bedazzled white gown with a fur shall, and she looked angelic. The strapless dress hugged her in all the right places.
We have always loved how confident Lizzo is in anything she wears, and she looked like she was beaming in this ensemble. She is one of those people who will continue to evolve and only get better with her style.
Lady Gaga - 2009
During her "Poker Face" days, Lady Gaga was not afraid to challenge fashion standards. She rocked her signature platinum blond hair with thick bangs and the drapey hoods that she paired with almost every outfit. It was definitely an interesting time in fashion.
However, Gaga has always been proud of her past looks because she set her own trends. Who else could get away with wearing a dress made out of raw meat to an award show? But her style has definitely mellowed out.
Lady Gaga - 2019
At the 2019 Oscars, Gaga wore this black gown with her hair in an updo, and it was far from what she would have worn at the beginning of her career. In 2009, Gaga never would have worn something so simple yet elegant, and we love this version of her.
She looks much more sophisticated now, but she is still not afraid to challenge fashion standards. Every once in a while, she throws in a more "out there" look to keep things interesting because she is still Lady Gaga after all.
Billie Eilish - 2016
Today, Billie Eilish is known for her over-the-top fashion choices, but it wasn't long ago that she wore rather normal outfits like this one to the Teen Vogue Young Hollywood party. The green t-shirt dress with a camo hat and braids was nothing to write home about.
To be fair, Eilish was only 14 when she first shot to fame for her song "Ocean Eyes," so it is not surprising that she kept things simple and casual at the beginning of her career. However, things have definitely changed since then.
Billie Eilish - 2020
After a few years in the industry, Eilish started to make much bolder choices with her outfits and hair color. For a while, she had these neon green roots with black ends that many people tried to recreate. She also experimented with many different designer outfits.
For the 2020 Oscars, she wore this oversized Chanel suit with extra long black nails. Eilish has always been a fan of baggier clothing because she doesn't like to show off her body. However, she has made that work for her, and we can't wait to see how her style continues to evolve.
Jennifer Lopez - 2008
Jennifer Lopez has come a long way from her early days as a dancer in the '90s. However, the singer has always been into taking fashion risks and loves to show off her stunning figure. In 2008, she wore this low-cut white gown that elegantly hugged her body.
Around this time, she really started to step out of the box and try new looks because there was a period when her outfits were quite subdued. As she got more comfortable experimenting with her looks, she really turned up the heat with her fashion.
Jennifer Lopez - 2019
For the 2019 CFDA Fashion Awards, JLo rocked this Ralph Lauren set that showed off her toned abs. It was a moment that went down in fashion history. People couldn't help but look because the outfit is so iconic and extravagant.
JLo has had many show-stopping looks that will forever be remembered in fashion history. Each time she goes to an event, people look forward to seeing what she is going to wear. We hope she continues to turn heads with her unique and bold looks.
Victoria Beckham - 2007
Victoria Beckham, aka Posh Spice, can really do no wrong in our eyes regarding fashion choices. Back in the mid-2000s, she debuted what people coined the "Pob," a haircut only she could rock. She paired her bold blonde look with strappy dressed and bold patterns.
Before she had children, her style was all about daring choices and high-heels or sky-high platforms. It was something we could all appreciate, and it's what made her a style icon.
Victoria Beckham - 2019
Today, Beckham's style is much more toned down than it used to be, but she is still as chic as ever. Even when she wears jeans and a simple top, she looks elegant and put together. This all-black outfit may not be special or shocking, but she looks stunning.
As a mother of four children, Beckham opts for simpler fashion choices that can be dressed up and down. She also said she loves being able to wear more comfortable options compared to what she wore when she was a Spice Girl.
Sofia Vergara - 2007
In the mid-2000s, Sofia Vergara was still getting started in the acting world, and she dyed her naturally blonde hair dark brown to get more parts. She said that with her strong Columbian accent; people wanted her to look more Latina.
Regardless of her hair color, Sofia has always been a fan of cinched silhouettes with v-cut necklines. While she often wore similar looks, she always knew what worked for her body to show off her natural curves.
Sofia Vergara - 2020
While Vergara has stuck with the same silhouette throughout the years, she has never disappointed on the red carpet. Everyone wants to see her body, and she knows what looks good on her, so why change something that isn't broken?
It is pretty predictable what she is going to wear next, but that doesn't mean people are disappointed when she steps onto the red carpet.
Jennifer Lawrence - 2008
At just 17-years-old, Jennifer Lawrence was only just beginning her career, and she probably didn't even have a stylist. For one of her first appearances, she wore this blush one-shouldered dress and paired it with a pair of clashing grey heels.
We give her points for effort, but no one was thinking of her as a fashionista. For a while, she struggled with her looks and favored one-shoulder dresses. It was a while before Lawrence really got into the groove and figured out what looked good on her.
Jennifer Lawrence - 2020
Larence has definitely upped her game since the start of her career. In 2020 she attended a Dior fashion show in Paris and looked incredibly chic in an all-black outfit. She added a leather jacket for an edgy look that was far from what we saw in 2008.
The now 30-year-old has definitely figured out what kind of looks work for her. Lawrence also has a great stylist now, which helps her look perfect for every red carpet event.
Blake Lively - 2009
When Blake Lively was starring onGossip Girlas Serena Van Der Woodsen, her style was similar to her characters in that she wore simple yet chic outfits. For example, when she went to theGossip Girlpremiere in 2009, she wore this blue romper that is definitely Serena approved.
2009 was a time when people would have about 50 bangles on their wrist, and you could hear them coming from a mile away. We bet people always knew when Lively was approaching because she was a huge fan of those bangles.
Blake Lively - 2016
Blake Lively's style has only gotten better over time. But one thing we can say for sure is that blue is definitely her color. At the 2016 Cannes Festival, Lively donned this one-shoulder aqua gown that showed off her growing baby bump.
There has never been a look of hers that we didn't like, and we can't imagine Lively ever landing on a worst-dressed list. She always looks elegant even when she is wearing more daring things, and people are always excited to see what she will wear next.
Gwen Stefani - 2004
In 2004, Gwen Stefani stepped out on her own away from No Doubt and released her first solo studio album. Harajuku girls inspired her at this time, so many of her outfits had some nod to them. Although she had a quirky style, it worked for her.
This funky outfit was a fashion moment, and it showed off her toned abs. During this period, Stefani would wear Vivienne Westwood and John Galliano to show off her more feminine side.
Gwen Stefani- 2019
From rocking chaps, bra tops, and patched pantsuits, Gwen Stefani has once again leveled up her fashion game with a chicer approach. Today she still has fun with fashion but she wears more sophisticated silhouettes.
This structured high-low gown showed off her toned legs while still looking appropriate for the event. Besides her outfits, she also decided to stick with her platinum blonde hair after dying it every color in the rainbow during the '90s.
Jennifer Aniston - 2002
Jennifer Aniston became famous for her role inFriends, and many of her looks on the red carpet were inspired by her character Rachel Green. We can totally see Rachel wearing this simple tank and maxi skirt combo that showed off her abs slightly.
She always kept her outfits very simple, but they never looked boring. She has continued to get even more stylish throughout her career as the years go on, and she never seems to age. We would love to know what her secret is.
Jennifer Aniston - 2020
The beloved actress never misses the mark with her outfits, and she turns heads in even the simplest gowns like this satin one she wore to the Screen Actors Guild Awards in January 2020. Seriously, how does she do it?!
We have never hated an outfit Aniston has worn, and we don't think that will happen anytime in the future. She is always on-trend, and it's refreshing to see her refined style when she steps onto the red carpet.
Selena Gomez - 2008
If you have been a fan of Selena Gomez for a while, you already know that she can rock anything she wears. The former Disney Channel star has never shied away from experimenting with looks, but this blue dress was a safe choice for her at the time.
Around 2008, Gomez started to pick more sophisticated styles while still having fun with color and patterns. She soon became one of the hottest celebrities on the red carpet while trying different vibes and experimenting with edgy pieces.
Selena Gomez - 2020
After taking a break from the spotlight in 2016, she came back fiercer than ever with fashion choices that had people gasping. Although there was one hiccup at the Met Gala in 2018 because of a bad spray tan and poorly applied makeup, we forgive her.
For the annual Hollywood Beauty Awards in 2020, Gomez wore this pale pink strapless minidress with platform heels, and she looks as beautiful as ever. We are also looking forward to seeing what she is wearing because we love to take inspiration from her style.
Mila Kunis - 2008
Mila Kunis has been walking red carpets since she was a teenager and starred onThat '70s Show. In 2008, Kunis had roles inForgetting Sarah MarshallandMax Payneunder her belt, so she was a master at walking the red carpet.
Kunis rocked looks like this sequined Stella McCartney sheath dress and black pumps for a VH1 event. She has never been one to play too much with fashion, but she always looks stunning in whatever she wears.
Mila Kunis - 2018
In recent years, Kunis has stuck with her signature sleek style. While there is no shortage of killer glam looks, this simple suit style, worn to theSpy Who Dumped Me screening, stands out because it is more mature and different from what she normally wears.
Kunis always looks perfectly put together, even when she is running around with her kids and handsome husband, Ashton Kutcher. She has come a long way from her teen years, and she is another person to look to for outfit inspirations.
Kiera Knightly - 2007
After starring inPirates of the Caribbeanwith Johnny Depp, Knightly was one to watch on the red carpet. For the movie premiers, she would experiment with edgy dresses and styles, but this was a subdued look for her during that time.
While we have nothing wrong with a ballerina-esque dress, the black and silver strappy pumps are throwing us off. It seems like she was having a bad style day here, but we are glad she recovered from this look.
Keira Knightly - 2018
Today Knightly's style is much more toned down than it was in the past. The actress wears much simpler silhouettes than she did in the early 2000s, but she always looks chic. This blue dress is definitely a more conservative number, but we don't hate it.
While her style is simpler than usual, Knightly looks lovely in everything she wears. Throughout the years, she has changed so much since her peak popularity.
Beyonce - 2006
After going solo and leaving Destiny's Child, Beyonce did not disappoint with her red carpet looks. At the 2006 premier ofDream Girls, Queen Bey turned heads in this floaty gown.
The singer looked stunning in the blush pink dress with delicate beading. She was every bit a leading lady, and her style only got better over time.
Beyonce - 2019
Beyonce has rocked many iconic looks throughout the years, including this gold dress that she wore to the premiere ofThe Lion King. She looked statuesque and stood out on the golden carpet even though she matched it.
Beyonce is the ultimate glamazon, and she always serves all the diva attitude we are craving. Each year, we look forward to what she will wear for the biggest events like the Met Gala or the Grammys.
Rihanna - 2007
Rihanna's style has evolved quite a bit since she made her debut in 2005. At the beginning of her career, she opted for simpler styles like subtle dresses or casual ensembles that showed off a lot of skin.
Since releasing her debut single "Pon de Replay," Rihanna has made many musical twists and turns, but her fashion sense is always on point. She has definitely played more with her hairstyles, which haven't always been our favorite, but they work for her.
Rihanna - 2018
Since taking a step back from the music industry to focus on her makeup and lingerie business, she has evolved into a boss lady. At the premiere ofOcean's 8, she wore this head-turning gold number and proved she is on top of her fashion game.
Rihanna paired her dress with a matching clutch and topknot bun style that wowed everyone around her. One thing we know for sure is that the singer will never stop experimenting with her style and rocking every look she puts on.
Anne Hathaway - 2007
Following the success of The Devil Wears Prada, Anne Hathaway was riding a high because she was a household name that continued to impress fans. The starlet already had quite a few red carpets under her belt at this point, and she was still learning what her style was.
For the 2007 Vanity Fair Oscar party, Hathaway wore this bow-adorned Valentino Gown that wasn't quite right for her skin tone and didn't do much for her body. While she looked beautiful, it would be some time before people looked to her as a fashionista.
Anne Hathaway - 2019
As the years went on, Anne Hathaway experimented with her style and rocked some killer looks. Whether she is receiving an award or not, she never fails to bless us with unforgettable fashion moments like this fierce metallic leopard print dress she wore in 2019.
The risky look is not one that many people could pull off, but Hathaway did it so effortlessly. She proved that you can never have too much animal print. Hathaway has come into her own and is always one to look for on the red carpet.
Miley Cyrus - 2007
Miley Cyrus was just 13 when Hannah Montanadebuted, so her early red carpet looks weren't always the most fashionable. She was more innocent back in the day with her natural brown hair and conservative fashion choices.
One thing we can say about Miley Cyrus is that there weren't many early looks of her that we hated. However, she did go through the Disney phase, where she layered every tank top and t-shirt in her closet over leggings and a skirt, so her style needed some improvement.
Miley Cyrus - 2019
No one can forget the dreaded period where Miley Cyrus chopped off all her hair after her first breakup with Liam Hemsworth. It was a sad time for hair and fashion, and we are glad Cyrus was able to pull through this strange period.
Starting in 2016, we saw Miley rock some unforgettable fashions and better hairstyles. One of our favorite looks was this simple black suit she wore to the 2019 Grammys. It was a chef's kiss in our fashion books and we hope she stays on the style streak.
Emma Watson - 2002
Although Emma Watson was just 11 at the time, she was pretty fashionable for a pre-teen. At the premiere ofHarry Potter and the Chamber of Secrets, Watson chose this brown leather blazer, a shimmering tank top, and a matching bag. We hope she kept this outfit because it's back in style now.
While we can't say she hit the mark on every look throughout the years, her style was never terrible. However, she did wear flats at many movie premieres, and they didn't always go with her outfits.
Emma Watson - 2019
Fast forward to 2019, and we can wholeheartedly say that Watson has killed it with some looks throughout the years, like this dress she wore to theLittle Womenpremiere. As she got older, Watson was never afraid to try daring looks or step outside the fashion box.
Even when she chopped her hair into a pixie cut to shed her Hermoine Granger look, we still loved her style. Is there anything Emma Watson doesn't look good in? We can't wait to see what she will wear next!
