Caitlyn Jenner Vs. Kris Jenner
It is bad enough when the celebrity that you end up twinning with is a friend or a complete stranger, but when it is your ex, it is even more important to know who looked better in it. This happened to Caitlyn and Kris Jenner.
In early 2020, Kris had an appearance on a popular British TV talk show and wore a simple yet elegant black dress with a gold zipper. Eight years previously, Caitlyn had worn the same or similar dress to a publicity event.
Gigi Hadid Vs. Bella Hadid
Sibling rivalry isn’t just reserved for the Kardashians on this list – the Hadid sisters seem to enjoy wearing the same outfit as well – and it’s hard to pick a winner for this one.
Both Hadid sisters were seen out and about wearing this Tommy Hilfiger silver puffer coat. Gig kept it very ’90s with a turtleneck and jeans, while Bella was seen wearing it a few months later with more of an athletic look. Let’s be honest, they’re both stunning no matter what they wear.
Miley Cyrus Vs. Harry Styles
Fashion knows no gender, and that means that sometimes you will be competing with the opposite one, just like Miley Cyrus and Harry Styles did in this black sequined jumpsuit.
In 2019 at the Oscar party for Vanity Fair, Cyrus strolled down the carpet in this chic little number, and a short while later, the former One Direction member rocked it at his SNL performance. The two even seem to have the same accessorizing thoughts too. Both definitely looked good.
Jameela Jamil Vs. Jonathan Van Ness
Rocking the runway at the Netflix Creative Arts Emmy’s afterparty, Jonathan Van Ness, one of the stars of Queer Eye, rocked this stunning fuchsia trapeze dress.
The strapless number designed by Rochas was also the same dress worn by the British comedic actress Jameela Jamil at a YSL party in late 2019. No need for users to choose, Jameela copped to the fact that Jonathan wore it better on Twitter.
Kim Kardashian West Vs. Winnie Harlow
This entry from one of the Kardashian clan members is going up against Winnie Harlow. Both took a spin around town sporting this green Maisie Wilen dress.
Kim opted to tie in the yellow accent with a pair of strappy sandals. Having the same thought, Ms. Harlow chose to pick up the accent by matching her clutch to the yellow. Neither of them did any harm to this dress. In fact, they both kind of slayed it.
Brooke Burke Vs. Sofia Vergara
It is pretty common nowadays for stars to create their own fashion line. When they do, what better a way to get some free publicity than to wear it out and about on the town yourself?!
Sofia Vergara did that with a cut midi dress from her Sofia jeans by Sofia Vergara line. Then just a few months later, Brook Burke was spotted attending a meeting wearing the same dress.
Victoria Beckham Vs. Megan Markle
It might not seem fair to ask who wore it better when one of the participants is clearly pregnant, but when you’re a star, all bets go out the window when it comes to fashion.
So when Meghan Markle stepped out in the same dress as Posh Spice herself, Victoria Beckham, there were sure to be some comparisons. Both chose colored accents, but Posh’s accent is just a bit brighter.
Zendaya Vs. Gwyneth Paltrow
Zendaya has come a long way since her Disney days and has cemented herself as quite the fashion icon (hence why she is on our list more than once).
In early 2020 at one of the many awards ceremonies on her to-do list, Zendaya rocked a Tom Ford metallic breastplate. That same piece was also worn by Gwyneth Paltrow on the cover of Harper’s Bazaar just a month later.
Michael B. Jordan Vs. Zendaya
The unisex look is something that not everyone can pull off, but Zendaya definitely seems to have it down to a tee. She sported a charcoal grey suit from Berluti to a Harper’s Bazaar event that had previously seen the red carpet on the back of Michael B. Jordan.
Being the gentleman he is, Michael answered the question before we even asked via twitter. His opinion? Zendaya, all the way!
Khloe Kardashian Vs. Kylie Jenner
The sisters of the Kardashian/Jenner household seem to like to strut their stuff in the same things. This just begs us to compare them with each other, like in this animal print one-piece.
The one-piece from Onia x We Wore was donned by the younger sister on her trip to Turks & Caicos. There, she posed for a few ‘grams. Not to be outdone, just a few months later, Khloe sported the same suit on her trip, posting an image to Instagram as well.
Kristina Schulman Vs. Danielle Lombard
The Bachelor is a phenomenon that has gone on for seasons, and many of the past alums have made quite the name for themselves. Two of these attended the same party and wore the same dress.
This could have been the height of embarrassment, but both rocked it their own way. Kristina chose to go business and accessorize it with a blazer and booties, whereas Danielle decided to go a little more hip and pair it with a leather jacket and white sneakers.
Kourtney Kardashian Vs. Kim Kardashian West
Fierce is one word some would use to describe the Kardashian sisters, and in this case, they would not be wrong. Both Kim and Kourtney chose to wear this tiger printed Roberto Cavalli dress.
Kim sported it first, and then a few months later, the elder sibling attempted to show her how it was done. Which sibling did it serve better? That is up to them, and hopefully, it doesn’t lead to another catfight.
Rihanna Vs. Bella Hadid
Bella Hadid walked the runway and took fashion to the races with this checkerboard cape and short pairing. She definitely worked it on the runway. A few months later, another star worked it maybe just a little harder.
Rihanna, the pop icon, loved the look so much she took it out for a spin to a concert. This concert was on her home island of Barbados, and she lit the night on fire in this fantastic ensemble.
Amanda Peet Vs. Meghan Markle
Even when you are pregnant, you still want to look pretty, and especially when you are holidaying in Morocco. Duchess Meghan Markle chose to do that in a blue Carolina Herrera dress.
That same dress found its way to the Game of Thrones season 8 premiere. This time it was worn by actress Amanda Peet with a bit of a different fitting, of course. The glow that Meghan had changed everything, and for this one, she may have had a little bit of an advantage.
Travis Scott Vs. Kanye West
There are plenty of men who like to show off their fashion abilities, and one of the biggest is Kanye West. During his 2011 Coachella performance, he sported this Celine top without ever breaking his swag.
That same shirt was thrown over a simple white tee seven years later by Travis Scott, and still, the shirt screams “I know how to dress.” Both rappers understand how to leave their mark when it comes to fashion.
Zendaya Vs. Timothee Chalamet
The Euphoria stars seem to have a similar style when it comes to red carpet events. Zendaya, a few years ago, chose to wear a beautiful fuchsia Christian Siriano suit to a Humane Society event.
Inspired by this bold and stylish look, her now co-star Timothee Chalamet opted to wear something very similar. This time, the hot pink suit was designed by British fashion designer, Stella McCartney. Both clearly have a wicked eye for style.
Priyanka Chopra Vs. Olivia Wilde
Both of these stunning actresses know what looks good on them, and apparently, the same printed Kate Spade dress is one of those things. Olivia Wilde chose to go with a bolder color, making her modeling of this dress a little more memorable.
But Priyanka wasn’t to be outdone, choosing to go a little more subdued with her color choice (despite being able to rock that bright pink very well). Both have a keen eye and looked stunning in the dress.
Tracee Ellis Ross Vs. Jackie Aina
Dior has been a name in women’s fashion for decades, and so everyone wants to wear a piece when they go out on the town or to a special event.
So when this fly leather cage skirt found its way into the hands of both YouTube star Jackie Aina and the comedic actress Tracee Ellis Ross, there were bound to be some arguments over who wore it with better vibes. Tracee chose to wear the skirt a little more business chic than Jackie, but both got it right.
Jennifer Garner Vs. Meghan Markle
Another entry from the Duchess herself, Meghan Markle. This time she wore a beautiful navy Roland Mouret dress to an event the night before her illustrious wedding. She accessorized the dress with simple jewelry and tasteful pumps.
Just months before, Jennifer Garner wore that same dress as she accepted her place on the Hollywood Walk of Fame. The actress chose to go without any accessories.
Dua Lipa Vs. Gigi Hadid
There are just some names that are synonymous with fashion, and one of them is Versace, hence the iconic and classic reputation of the designer and his clothes. That is why, no matter the age, if you want to look fabulous, investing in a Versace piece is a good bet.
Dua Lipa and Gigi Hadid know this, as is evident by their choice to rock a multi-colored jumpsuit. Gigi wore it first on the carpet at a fashion awards show. But Dua chose to wear it out for a fun night in New York City. Both know what they’re doing when it comes to fashion, that is for sure.
Leona Lucia Vs. Chiara Ferragni
It is rare that you get a mother-son “who wore it best?”, but here you have it. Fashion influencer Leone Lucia chose to take the question to her Gram. There, she posted this image of both wearing the same t-shirt.
The cute novelty tee from Fiorucci looks great on both, but we think Chiara has the better model pose, so he clearly wins the contest. Plus, he is just plain adorable.
Olivia Munn Vs. Mary J. Blige
Who are you wearing? Fendi, of course, was the response of both Mary J. Blige and Olivia Munn. Both chose to take this black and white jumpsuit out on the town. Mary J. sported hers to the Essence Festival and paired it with a pair of matching peep-toe pumps.
Olivia, on the other hand, chose to go a little more relaxed. But no matter how the outfit was worn, it looked great on both of these amazingly beautiful ladies.
Demi Lovato Vs. Whoopi Goldberg
Did Whoopi inspire Demi? Who knows, but both hit the red carpets strutting their stuff in this cheetah print Dior gown. Goldberg wore it to the 2009 Oscars and Lovato nine years later at the Billboard Music Awards.
There is a little difference, of course – one wore a belt and let their legs slip through a slit, and the other went for a more covered-up look. Neither was wrong, and both were fun.
Beth Behrs Vs. Emmy Rossum
A simple little black lace top can be quite the addition to any outfit, but these two actresses took that idea to a whole new, yet very simple level. Emmy Rossum chose to don this number at a very special book launch.
Just a few days later, Beth Ehlers from 2 Broke Girls took the same top on a spin down the red carpet to a Hollywood premiere. Both paired it with a high waisted pair of pants and some cute pumps.
Helen Mirren Vs. Nina Dobrev
Seasoned veteran versus new blood? A generational “who wore it best?”. The iconic veteran actress Helen Mirren took a spin in a Prabal Gurung with ruffles to a film premiere. Keeping it classy, she paired it with a gray heel and a perfect little clutch.
As an alternative, the young star of Vampire Diaries, Nina Dobrev, wore the same dress to her premiere of Flatliners. She took a little more edge to it and paired it with a set of strappy jeweled pumps.
Storm Reid Vs. Zendaya
Zendaya, as we have already said, loves a good pantsuit, so when it came time to collaborate with the world-class designer Tommy Hilfiger, she had to include one in her line, and show it off.
A little while later, the young star of A Wrinkle in Time, Storm Reid, chose to rock the same suit. She decided to make it a little more dressy by throwing the blazer over her shoulders.
Meghan Markle Vs. Courtney Love
Meghan Markle and Courtney Love don’t have a lot in common except for their fame, and maybe a bit of style. The two ladies both put on a classy black Stella McCartney coat as they went out on the town.
The Duchess wore hers on a trip to Wales, while the rocker chose to wear hers at a YSL event in Paris. Both wore it well and chose to style it in their own unique ways.
Blake Lively Vs. Busy Philipps
Tartan is a fabric that has a classic and chic look, no matter how it is worn. Busy Phillips thought she would try on a Brunello Cuccinelli suit that Blake Lively had taken out on the town a few months previously.
Busy chose to let the suit do the talking, whereas Blake opted to top it with a long leather trench. Both took their own style and made the suit work for them.
Emma Roberts Vs. Alessandra Ambrosio
Both of these young celebrities decided to show their support for women’s rights and power by pairing this comfy t-shirt with denim. The style was not chic, more of an everyday wear kind of situation.
But, both Roberts and Ambrosio were still able to make the shirt their own by pairing it with different denim types. That pretty much makes this contest a wash.
Kat Graham Vs. Katy Perry
The musician vs. actress “who wore it best?” lives on when it comes to this rainbow sequined dress from Christopher Kane. Katy Perry decided this was the look she wanted to strut on an appearance on a morning talk show.
On the other hand, the actress Kat Graham (who, by the way, is also a musician) took the same look and paired it with a different shoe for a more relaxed look. Don’t get us wrong, she still looked chic. It was just a little less flashy than the red pumps that Perry wore.
Michael B. Jordan vs. Zendaya
A sleek suit is definitely the one thing you don’t want to miss out on in your closet. This suit comes in two different colors (or at least these two put it in two different types of lighting). It looks like Michael B. Jordan took a deep charcoal gray while Zendaya chose a deep gray-blue.
Both of these stars kept this suede suit simple and buttoned with a dress shirt underneath and a tie to complete the look. But there’s something about Zendaya’s stance with one leg out slightly and a hand in the pocket that definitely seems to set it off right.
Kendall Jenner vs. Rita Ora
This tunic-style dress is one that creates a statement on its own in a monochromatic black and white. The deep V of the neckline is a little bold but still conservative enough to be worn without anything under it, like Kendall decided to do. Or you can add something under it like Rita.
While Kendall kept things simple with a straight hairstyle and no accessories, Rita paired a fishnet style shirt under this tunic as well as fishnet stockings. And the bold makeup and braids definitely complete the look.
Beyonce vs. Keke Palmer
These two had some spectacular fashion sense with their Yousef Aljasmi gowns for two different formal events. The form-fitting gold dresses most definitely turned heads, and these two women knew how to pull off all of that sparkle and then some.
Beyonce paired her version with a cute clutch and some bright, shiny earrings while Keke kept things a little more subdued. Though her bright white nail polish definitely set off the dress as well.
Nicky Hilton vs. Ashley Benson
This leopard print jacket definitely pairs well with an all-black ensemble and both of these women knew that when they ventured out with it. Matching black bags, black leggings, and of course their long blonde, hair make it difficult to determine just which of these two pulled off the best look.
While Nikki kept her jacket all buttoned up, Ashley chose to leave it wide open to show off the perfect clothing choice underneath. Not to mention the oversized sunglasses that really pull off that casual style.
Doutzen Koes vs. Gwen Stefani
These two rocked out in the same David Koma dress, but in two completely different colors. Black and white are an excellent complement to one another, with a sleek, monochromatic look, and maybe these two are both the winners in this dress.
Doutzen chose strappy sandals and no accessories for her rendition (though the beachy waves in her hair might be considered an accessory). Gwen instead chose some more classic pumps and plenty of silver bangles to make the look her own.
Rosamund Pike vs. Meghan Markle
The Duchess definitely knows how to dress and this outfit by Emilia Wickstead is no exception. She chose to pair the black version of this button-down dress with a cute hat and pocketbook for a royal occasion. On the other hand, Rosamund Pike chose the white version without the accessories.
Both dresses give a springtime look and accentuate a smaller waist. Not to mention all those buttons down the front that really set off the look. These monochromatic twins definitely make it difficult to decide who did the best job.
Jennifer Lopez vs. Kris Jenner
With this dress, you’re definitely going to get all the attention. The high neck, long sleeves, and long skirt make it more conservative, but that slit up the side and the glitter all over definitely make sure you’re going to be noticed. And that’s exactly what Kris Jenner and Jennifer Lopez both did.
J Lo decided to create an intricate updo with simple stones at her ears. On the other hand, Kris chose a little more glitz for her jewelry, including rings and bracelets, and kept her short hair more simply styled.
Miley Cyrus vs. Lena Dunham
Between these two, this pantsuit definitely makes an impression. Miley chose to wear it in a slightly baggy style, while Lena went with a slightly more fitted look. But both pulled off the casual, hands in the pockets routine when it was time for the photos.
The all-black of the pantsuit itself is slimming and yet still bold, but it’s the white stripe across the top that really sets it off. Both of these celebs chose to keep the jewelry practically non-existent, with Miley pulling out only a single bracelet on each wrist for the occasion.
Tracee Ellis Ross vs. Jackie Aina
This unique black skirt is definitely one way to make a statement. The black color means that it pairs with anything and the woven design gives it just the right hint of style. Tracee chose to pair hers with a black top and black jacket along with a gold necklace and clutch.
On the other hand, Jackie chose a black dress shirt, tucked in for a bit more professional look, and a statement bag. But the all-black style for both is definitely sleek and oh so gorgeous.
Zoe Saldana vs. Kim Kardashian
This mauve colored dress features casual straps and a straight neckline with a cinched waist and a slightly full (but short) skirt. It’s definitely the kind of dress you can wear to an event like Saldana, or out for a stroll like Kim.
Both paired the dress with some more classic pumps but with a little bit of a strappy look. Plus their long dark hair really complimented the fact that this dress bares a little bit more of their shoulders. Why not show off those great locks?
Reese Witherspoon vs. Paula Abdul
This play on a schoolgirl outfit (or maybe it’s a nuns habit) definitely has some fun to it. The black dress with white accents creates its own style. Perhaps that’s why each chose to pair it with simple accessories like Reese’s pearl and gold earrings and Paula’s fishnet style stockings.
The end result is a somewhat demure dress, that still gives a bit of edgy vibe. After all, they’ve each got their own style to rock, right? And for any event, this dress really does make an impression.
Shakira vs. Pink
These two rocked out with the same dress at the MTV Awards and both of them definitely knew what they were doing. This leather look dress creates a unique vibe and the short, strapless, fitted style definitely showed off their own personal styles. Pink chose to pair it with pumps while Shakira went with tall black boots to complete the look.
It’s definitely a look that fits the MTV awards, and wouldn’t look out of place in a nightclub either. Not to mention it pairs great with the short punk hairstyle Pink has and the long, messy waves that Shakira is rocking.
Lady Gaga vs. Beyonce
This see-through red dress definitely does have its own flare and both Lady Gaga and Beyonce chose to take it on in slightly different ways. Lady Gaga chose a black bodysuit under the sheer dress while Beyonce paired it with even more red for a vibrant look.
Lady Gaga pulled her hair back into a more severe look with her small sunglasses and hoop earrings. Plus some chunky boots and stockings. On the other hand, Beyonce chose her signature curls hanging down her shoulders with sunglasses and some strappy silver heels.
Miley Cyrus vs. Taraji Henson
The little black dress is a staple in just about any closet and there’s a reason for that. But Miley and Taraji took that a step further with this dress. The sleek black looks stylish while the cutouts definitely create a little more enticing look to go along with it.
Miley paired this floor-length gown with a slicked back, short hairstyle. On the other hand, Taraji chose to keep her long, dark hair down around her shoulders, highlighting the dress and those curls at the same time.
Kate Middleton vs. Drew Barrymore
These two definitely have something in common with the auburn hair and the same taste in fashion. While Drew chose to keep the dress plain, the Duchess chose to pair it with some cute earrings and a shawl to stay a little warmer.
There’s no end to the bright colors with this one, which means it attracts just the right amount of attention, and the slit down the front has a sort of peek-a-boo look that’s still plenty conservative for an audience with the Queen (or anyone else).
J-Lo Vs. Shakira
There are few celebrities that can stand up to the style icon J-Lo, but at the Superbowl in 2020, Shakira sure tried her best. Though not exactly the same outfit, there were enough similarities to compare the two.
J-Lo rocked a silver Versace fringe jumpsuit while the Colombian hip shaker, Shakira, opted for a gold option. They both kind of worked it, so why don’t we call this a draw, shall we?
Meghan Markle Vs. Lupita Nyong’ o
It is hard to compete with stunning beauty like the Oscar winner Lupita Nyong’o, but the Duchess of Sussex thought she would try. At a music festival in March 2020, Meghan Markle donned a beautiful red caped dress designed by Safiyaa.
This dress was very similar to the one that Lupita had worn in 2014. Though Ralph Lauren designed Lupita’s version, the lines and shape were similar enough to stir some comparisons.
Emily Ratajkowski Vs. Gigi Hadid
The Tony Awards are a good occasion to get out the fancy duds and show off what is new in your wardrobe. When it comes to fancy duds, there is nothing like an elegant black dress. Which is exactly what model/actress Emily Ratajkowski thought when she rocked this number.
The dress, though, had been snapped on the runways of 2019’s spring and simmer lines. Who rocked it? Gigi Hadid. And she did a pretty good job – not to say Emily didn’t hold her own.
Beth Stern Vs. Molly Sims
One may not think of cat print as an actual cat picture. Some would even question if this print is even stylish, but when paired with the right person, even a dress with cats all over it can be quite chic.
This is what happened with this midi dress that both Molly Sims and Beth Stern chose to wear out and about. Both chose to accessorize it differently, and this made them both fashion winners.
Kim Kardashian West Vs. Kylie Jenner
Sisters often share closets, but it seems like there is a rotation going on in the Kardashian/Jenner girls’ homes. They have found themselves on this list several times already.
This time, it is a faceoff between Kim and Kylie. Both were seen in public wearing a very cute halter top from Charlotte Knowles. Kim strutted her stuff on Instagram, showing off her look with this top. Then later that evening, Kylie hit the streets to have a fun evening in the same top.
Oh no, she’s wearing the same outfit! This is a catastrophe! While wearing the same outfit to the same event is a major faux pas, there is nothing wrong with wearing the same thing in public, right? Yes and no! It is just another funny anecdote for regular people, but when you’re a celebrity hitting the town with the same thing on as another celebrity, it only serves to ask the question of who wore it better. We have found a few instances like this, and we are going to take a look at just who rocked it the best!