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Harry Styles and Kendall Jenner's Relationship: A Look Back

Harry Styles and Kendall Jenner were romantically linked from 2013 to 2019

Keeping Up with the Kardashians star Kendall Jenner and Harry Styles were romantically linked multiple times from 2013 to 2019.

Although they never confirmed their relationship, the model and singer share quite a romantic history, including taking trips on Ellen DeGeneres ' yacht and going on ski vacations for New Year's. Jenner and Styles even enjoyed a memorable "meal" together when the former One Direction member filled in for James Corden as host of The Late Late Show in December 2019. During their appearance, the two looked like old pals while playing Corden's "Spill Your Guts or Fill Your Guts" game.

From casual nights out to sharing secrets on late-night TV, here's a look back at Harry Styles and Kendall Jenner 's relationship through the years.

Nov. 20, 2013: Harry Styles and Kendall Jenner have a date night in West Hollywood

In 2013, following his split from Taylor Swift earlier in the year, the pair shared dinner at Craig's restaurant in West Hollywood and were photographed leaving the restaurant in Styles' car. The meeting sparked rumors of romance that both parties were quick to deny. "They're just friends," a source told PEOPLE at the time, while Kendall assured everyone on Twitter that she was, indeed, single.

Flash forward to Dec. 1, 2014, when the pair hung with pal Cara Delevingne (pictured above) at the British Fashion Awards at the London Coliseum, again sparking rumors of a romance.

Jan. 1, 2014: Harry Styles and Kendall Jenner go skiing together

On New Year's Day in 2014, Styles and Jenner were spotted skiing and snowboarding in Mammoth, California. According to reports, the duo stayed in a house with a group of friends, though they appeared to be coupled up. A source told PEOPLE of the excursion, "Kendall snowboarded and Harry skied. They were very cute together. There was a lot of flirting and smiling going on." They also said, "Harry was a gentleman and even offered to carry Kendall's snowboard to the ski lift." Talk about a winter wonderland!

Dec. 29, 2015: Harry Styles and Kendall Jenner go on a Caribbean vacation to celebrate the New Year

Styles and Jenner ushered in another new year together two years later when they vacationed in Anguilla in the Eastern Caribbean. The pair were spotted by fans at a restaurant on Dec. 29, 2016, and later seen getting cozy on a yacht . A source told PEOPLE, "There has been a lot of flirting, touching and snuggling going on. They have acted like a couple. They look very cozy and happy."

Jan. 2, 2016: Harry Styles and Kendall Jenner board Ellen DeGeneres' yacht

They continued their vacation when they boarded Ellen DeGeneres and Portia de Rossi's yacht in St. Barts on Jan. 2, 2016. A source told PEOPLE that "things never got serious" between the two when they first met, adding, "He has thought all along that Kendall is hot and was sort of just waiting for a chance to spend more time with her again."

The source also said of the trip, "New Year's worked out perfect, and [Harry] loved it."

Jan. 7, 2016: Khloé Kardashian says Harry Styles and Kendall Jenner are dating

Gotta love when big sisters blow up your spot! Khloé Kardashian said she thought the pair were dating, telling Entertainment Tonight , "They were hanging out together. Do I think they're dating? Yes. I don't know if they're like boyfriend-girlfriend. Nowadays, I don't know, people are weird with stuff. So I don't know their 'title,'" she said, using air quotes. "But I mean, they were in St. Barts together hanging out, so to me that's dating. I would call that dating."

She added that she wasn't sure if they had defined the relationship admitting, "I don't know if they've had that talk yet."

Jan. 23, 2016: Harry Styles and Kendall Jenner attend the same party in West Hollywood

Jenner and Styles attended a private party celebrating music agent Jeff Azoff's birthday at the Troubadour rock club in West Hollywood, California, on Jan. 23, 2016. Jenner's mom, Kris Jenner , and Styles' stepdad Robin Twist were also in attendance.

According to E! News , the Jenners arrived at the club about an hour after Styles and spent another hour inside before leaving. Styles reportedly left the venue later in the night.

April 8, 2016: Harry Styles and Kendall Jenner may have been spotted shopping together in L.A.

A fan claimed on Twitter that Jenner and Styles were seen shopping in Los Angeles together with a group of friends. However, the sighting came just weeks after PEOPLE confirmed Jenner was dating Lakers player Jordan Clarkson and had been for months.

Sept. 1, 2016: Harry Styles and Kendall Jenner have dinner in L.A.

Styles and Jenner were spotted on a date in L.A. on Sept. 1, 2016, with an onlooker saying Jenner was "beaming all night." A source told PEOPLE exclusively the following week that, after getting cozy over the holidays, the pair were "rekindling their old romance," and Jenner was "so excited and happy about it." The source added, "She's always cared about Harry."

September 2016: Harry Styles and Kendall Jenner are "not officially back together"

Styles and Jenner were rumored to be giving romance another try, but the two were taking things slow according to a source.

The source also said Styles and Jenner were "not officially back together" but were "continuing to talk and see where things go."

Jenner remained "hopeful" about her rekindled relationship with Styles but was also "being more careful this time," added the source.

"He's not going to settle down, and she understands that's just the way he is," said the source. "She really likes him, but her heart's not as invested."

Nov. 2, 2016: Harry Styles attends Kendall Jenner's 21st birthday party

Three of Jenner's rumored love interests showed up for her 21st birthday bash at L.A. hotspot Delilah, and Styles was among those in attendance at the star-studded affair. The guest list also included NBA player Clarkson and rapper Travis Scott (though Scott would begin a relationship with Jenner's younger sister Kylie Jenner just months later).

A source told PEOPLE Jenner wasn't with any particular guy and spent equal time with each of them.

"She worked the room and spent a lot of time with Travis in the beginning, then went to Harry for a while," said the insider.

April 18, 2017: Harry Styles hints that his debut album was inspired by Kendall Jenner

In 2017, the "Adore You" singer had fans buzzing when he seemed to allude to his relationship with Kendall in a Rolling Stone article . While talking about his debut, eponymous album of the same year, he mentioned the woman that inspired him. "She's a huge part of the album," he told the magazine. "Sometimes you want to tip the hat, and sometimes you just want to give them the whole cap … and hope they know it's just for them." Could it be that the songs on the album were about Jenner?

May 6, 2019: Harry Styles and Kendall Jenner reunite at the Met Gala

It's not uncommon for celebrities to reunite at fashion's biggest night , but a picture was worth a thousand words when Kendall and Harry were spotted having a conversation inside the event in May 2019. The pair didn't end the night there. In fact, they didn't end the night at all — they joined some other pals and kept the party going well into the next morning, and were spotted leaving an afterparty around 6 a.m.

At the time, a source told PEOPLE that they weren't an item and confirmed that Kendall was still seeing her then-boyfriend, Philadelphia 76ers player Ben Simmons .

The source said of Harry and Kendall, "Harry was her first real relationship, so there is a lot of history there," adding, "but they're just friends."

Dec. 10, 2019: Harry Styles and Kendall Jenner spill their secrets on The Late Late Show

Fans were sent into a tizzy when the pair hung out on camera as Styles filled in for Corden on The Late Late Show and played the ever-so-enlightening game , "Fill Your Guts or Spill Your Guts." The easy chemistry between the two had many wondering if they were still an item or simply really great friends post-relationship.

At one point in the game, after reading the question to herself and admitting, "I'm dying to know this," Jenner asked, "Which songs on your last album were about me?" The audience cheered, but Styles chose to eat cod sperm rather than admit which tracks could be about the TV personality.

Nov. 14, 2022: Kendall Jenner attends Harry Styles' concert in L.A.

Jenner was seen enjoying a night out at Styles' concert with her sister Kylie Jenner and Hailey Bieber . The women were spotted smiling and dancing to Styles' music from the stands in videos shared on social media by concertgoers.

For the outing, the reality star wore a plunging snakeskin halter top while her sister and Bieber sported all-black looks.

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Kendall Jenner, Harry Styles Fuel Romance Rumors, Soak Up the Sun on a Yacht: Pictures

The model, 20, and the One Direction singer, 21, looked cozy as they soaked up the sun. Jenner showed off her runway-ready body in a bikini, while Styles shielded his shirtless torso under a towel.

Related: PHOTOS: The biggest boy bands ever

Earlier in the week, the Keeping Up With the Kardashians star was spotted dining with the boy-bander in Anguilla. The duo, who were first linked back in 2013, hit up a restaurant together on Tuesday, December 29.

A source tells Us Weekly the exes are “hooking up again” now that Styles — who also dated Jenner pal Taylor Swift — has some time off from 1D. Adds another insider: “Now that he has a little hiatus and is on vacation, this is him trying to win her back, and it appears to be working.”

The second source notes that while Styles was the one to call it quits back in 2014, he was drawn back after seeing her in the Victoria’s Secret Fashion Show. “All of his friends were saying how hot and amazing she looked,” the source tells Us.

Related: PHOTOS: Kendall rocks the runway

In any case, both seem to be enjoying the R&R — and Jenner in particular could use it. In a recent post on her app and website, she revealed that she was recently hospitalized for exhaustion, and that she was making a conscious effort to relax in the new year.

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“I guess my resolution would be to chill out more and have the ability to be a little more spontaneous,” she shared. “No matter what, 2016 is going to be the best yet. I can feel it!”

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Harry Styles

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Spotted: Kendall Jenner and Harry Styles Getting Handsy on a Yacht

The most flirty exes you'll ever see.

Update, 12/31: Well, here's another clue Kendall Jenner and Harry Styles may be on something more than just a friendly, platonic vacation in the Caribbean. The two were photographed on a yacht together in St. Barts, being exceptionally handsy. Harry was shirtless; Kendall was in a bikini.  Daily Mail posted pics that included Harry grabbing Kendall's wrists and feet , Kendall resting her model legs on him, and the two gazing right at each other, faces oh-so very close .

The most suspiciously flirty exes, indeed . Kendall's face says everything...

12/30:  Way back in the late days of 2013, Kendall Jenner and Harry Styles were rumored to be dating…or, as Harry clarified  in an interview , were dating- ish : "I mean, we went out for dinner, but no, I guess."

Fast forward two years, and the two are getting dinner together agaaain , this time on the British island of Anguilla in the Caribbean, E! reports   with  exclusive photos of the date. A restaurant-goer also confirmed it happened yesterday evening:

Soooo, is this trip a friendly get-together or a secret romantic getaway? Unclear , but here are some clues: Kendall Jenner is now a highly coveted top model, with a New Year's resolution to "find a boyfriend, but it's not legit at all, lol." Harry Styles is on hiatus from his five-boy-turned-four-boy band One Direction and is  on the market . 

And elsewhere, Kendall's close friends Justin Bieber and Hailey Baldwin are also on vacation, deliberately blurring the lines between love and friendship, playing with our minds, etc.: 

Alyssa Bailey is the senior news and strategy editor at ELLE.com, where she oversees coverage of celebrities and royals (particularly Meghan Markle and Kate Middleton). She previously held positions at InStyle and Cosmopolitan. When she's not working, she loves running around Central Park, making people take #ootd pics of her, and exploring New York City.

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Kendall Jenner and Harry Styles Definitely Celebrated New Year's Eve Together

There's an old saying — or one that's as old as season two of The OC — that the way you spend New Year's Eve is how you'll spend the whole year. If there's any truth to that, and there's always truth to The OC , 2016 is going to be the year of #Hendall.

Harry Styles and Kendall Jenner celebrated the last day of the year together on a luxury yacht in St Barth's.

They giggled.

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They whispered sweet nothings. ("I missed you this much." — Harry, probably.)

They wore jaunty hats...

...and matching circle-framed sunglasses.

They bathed in the sun sharing a single lounge chair. (Apparently no matter how luxury the yacht was, there was a shortage of lounge chairs.)

And they brought both of their mothers along for the fun.

Now that's a midnight toast we'd like to see. Where's the long-lens paparazzi when you really need them? (Just kidding, invasion of privacy is bad but witnessing Kendall, Harry, Kris Jenner, and Anne Twist ring in the New Year would be so, so good.)

RELATED: Harry Styles and Kendall Jenner Are Reportedly Spending New Year's Together

For more One Direction, watch these videos:

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Here's What Happened With Kendall Jenner And Harry Styles' Relationship

They're undisputedly two of the most beautiful people in the world, and frequently run in the same A-list Hollywood circles, so it makes total sense that Kendall Jenner and Harry Styles were a thing, even if their relationship was short-lived. 

As Grazia notes, the supermodel and former One Direction star were first linked back in 2013 and their initial dalliance was actually the beginning of Styles being linked with several Victoria's Secret Angels, including Sara Sampaio and Georgia Fowler. 

In the years since their romantic relationship ended, Jenner and Styles have remained close friends, memorably crossing paths at the 2019 Met Gala and even hosting a glamorous after party together. As Page Six reported, the fiesta was totally spontaneous, with an insider admitting, "The party came together very last minute. This was expected to be Harry and Kendall and a few close friends, but it became a huge group of A-listers." And evidently, there's still love between these two. 

Harry and Kendall were romantically linked for several years

The duo stepped out in public together again at the British Fashion Awards in London in December 2014, following it up with a New Year's vacation in Mammoth, California. An eyewitness described them as "very cute" and confirmed there was "a lot of flirting" going on. 

A couple years later, model Kendall Jenner and former boybander Harry Styles were snapped taking a vacation together, snuggling up on a yacht, and enjoying more intimate date nights. "They have acted like a couple," a source advised at the time. "They look very cozy and happy." During a New Year's 2016 celebration in St. Barts, an insider revealed Styles always fancied Jenner and was simply waiting for the right time to pursue a relationship with her.

According to People , following his highly publicized relationship with Taylor Swift in 2017, Styles was linked to Jenner again after the two were spotted sharing a romantic meal together and leaving the restaurant in his car in December 2019.

Although a source clarified they were "just friends" at the time and the "Keeping up with the Kardashians" star reiterated her single status, the rumor mill went into overdrive.

Kendall and Harry remain close friends

If anyone was confused and on the fence about if Harry Styles and Kendall Jenner were an item, the model's older sister Khloe Kardashian confirmed the coupling in 2016. "Do I think they're dating? Yes," Khloe told Entertainment Tonight  Kevin Frazier at the time. "I don't know if they're like boyfriend-girlfriend. Nowadays I don't know. People are weird with stuff. So, I don't know their title. But I mean, they were in St. Barts together hanging out, so to me that's dating."

Styles himself also seemed to hint at Jenner being the inspiration behind his 2017 debut album during a Rolling Stone interview, stating, "She's a huge part of the album," but by the release of the project, the relationship was already over. The former couple reunited twice in 2019, first at the Met Gala and then while appearing on "The Late Late Show with James Corden," per Entertainment Weekly . 

That same year, a source confirmed to Us Weekly that the two remained on excellent terms, noting, "Harry and Kendall are great friends and always have been." Although both of them remain super busy, so they don't hang out that often, the insider revealed, "When they do, they always have a blast. It's an easy, super chill friendship." 

As Glamour magazine notes, in 2021, Kris Jenner finally confirmed once and for all the duo had indeed been an item, during a virtual appearance on "The Ellen DeGeneres Show" – as if we didn't already know. 

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Serious Question: Why Are We Obsessed With Yacht PDA?

After Aperol Spritzing through Tuscany, Harry Styles and Olivia Wilde surfaced on a yacht this week. They kissed; they nuzzled; they possibly danced (or, alternate theory, simply clung to each other for balance). The couple, who met on the set of Wilde’s second directorial effort, Don’t Worry, Darling , even left their big boat so that an artfully mustachioed Styles could captain a smaller vessel through glittering Mediterranean waters. In my estimation, the Styles fandom lost at least a full afternoon’s worth of productivity to a forensic examination of this photo set. All I could think, to quote Courteney Cox in Scream 2 , was: It’s happening again .

After all, it’s July, also known as yacht season, an annual micro-season within summer in which super-celebrities and moguls embark on luxe floating vacations, often with sparkling, sexual overtones. Styles and Wilde join a long, storied tradition (one well documented on many episodes of The Ringer’s Jam Session podcast ) that includes Styles himself and Kendall Jenner, along with both of their mothers, off the coast of St. Barts in 2016. Beyoncé has been known to yacht dive from great heights (once from an aptly titled rental yacht named the Halo) on yachting jaunts with Jay-Z to Capri and Croatia. In 2019, Timothée Chalamet and Lily-Rose Depp ardently made out aboard a yacht off Capri, as Italy is the unofficial global epicenter of yacht season. After two terms in the White House, Barack and Michelle Obama decamped to David Geffen’s superyacht , the Rising Sun (or as he prefers, “R.S.”) in Tahiti, which is how we’d all decompress after eight years of Mitch McConnell if we could. 

It must be said that while the appetite and voyeurism for yacht-season photo evidence is strong, there are also persistent ethical questions about breaches of privacy. Yachts are at once one of the only places celebrities can be entirely alone—save for the prying eyes of long-lens paparazzi. And yet couples sunning and smooching are often accused of doing it for publicity, a murmur that Chalamet, for one, denied. In an interview with GQ , he recalled “waking up to all these pictures, and feeling embarrassed, and looking like a real nob .... And then people are like, ‘This is a P.R. stunt.’ A P.R. stunt ?! Do you think I’d want to look like that in front of all of you ?!”

There is something endlessly fascinating about yacht PDA, as well as platonic group yacht vacays (see: Oprah and Gayle King aboard the R.S. , on which Geffen notoriously quarantined) . Much of modern celebrity culture, from the aughties zenith of Us Weekly to the present, is predicated on a kind of imagined relatability. Stars—at least occasionally—are like us. They go to Starbucks, sometimes wearing Juicy jumpsuits. They walk their dogs. But most spectators will never find themselves lolling starboard, à la Styles and Wilde, on a yacht near Monte Argentario. It’s like glimpsing a Gatsby party from the other side of the Long Island Sound—not easy to look away. Of course, yacht-watching can border on grotesque. Amazon employees had to fight hard for their $15-per-hour rate; meanwhile, Jeff Bezos’s $500 million superyacht comes with a support yacht complete with its own helipad.

With the rise of Bennifer 2.0 , I can’t not think about the scenes from the now vintage “Jenny From the Block” video in which Affleck, in all of his pompadoured glory, caresses Lopez’s bikini bottom sur la mer . It was a bit of celebrity satire—a nod from two celebrities who never fail to feed the beast. In the spirit of second chances, here’s hoping for the real thing in 2021. 

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A Definitive Timeline of Kendall Jenner and Harry Styles' Relationship

Kendall Jenner and Harry Styles have a lot of "History." From vacationing in the Caribbean together to spending time apart, Jenner and Styles constantly keep the public guessing as to what's really going on between them. Now, a source tells PEOPLE exclusively that the two are back on after they were spotted on a swanky dinner date in L.A. on Thursday night. To recap, here's everything we know about the on-again, off-again romance between Styles, 22, and Jenner, 20. They grabbed dinner in November 2013 The two shared a low-key dinner at Craig's restaurant in West Hollywood and were photographed leaving together in Styles' car. "They're just friends," said a source. Jenner also took a moment to tweet that she was single.

Serious rumors started flying in 2014 The stars were first linked in January 2014 when they were seen going out to dinner and hitting the slopes at Mammoth Mountain in California. (At the time, Styles was 19 and Jenner was 18.) This was the first time they acted overtly couple-y in public. "Kendall snowboarded and Harry skied. They were very cute together. There was a lot of flirting and smiling going on," a source told PEOPLE . "Harry was a gentleman and even offered to carry Kendall's snowboard to the ski lift." Earlier this year, a source told PEOPLE that "things never got serious," despite their obvious connection.

RELATED VIDEO: See Behind-the-Scenes Moments of Kendall Jenner‘s Glam Life

In December 2015, they vacationed together in Anguilla Fans spotted them enjoying an intimate dinner together, and they were later photographed getting cozy on a yacht. The two appeared to be all smiles as they boated around the island and were even caught kissing.

A few days later, they hopped onto Ellen DeGeneres ' yacht in St. Barts, where they were again spotted looking quite couple-y.

Khloé Kardashian tried to explain her sister's relationship with the One Direction singer, saying that they were, in fact, 'dating' A few days after Styles and Jenner's New Year's getaway, Kardashian addressed their relationship status in an interview. "They were hanging out together. Do I think they're dating? Yes. I don't know if they're like boyfriend-girlfriend. Nowadays, I don't know, people are weird with stuff. So I don't know their 'title,'" she told Entertainment Tonight . But I mean, they were in St. Barts together hanging out, so to me that's dating. I would call that dating."

Same, Khloé. Same.

They went on a casual shopping trip in April 2016 The pair were seen shopping in Los Angeles. That January, after returning from their vacation, they had partied together at music agent Jeff Azoff's birthday celebration.

The two currently appear to be rekindling their romance On Sept. 1, 2016, Styles and Jenner were spotted on a dinner date at L.A. hot spot Tsabel, and an onlooker said that the model "was beaming" all night.

"They're rekindling their old romance and Kendall's so excited and happy about it," the source tells PEOPLE . "She's always cared for Harry."

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Harry Styles And Kendall Jenner Had A Very Revealing Dinner Date

Off a yacht and into the deep end, because Harry Styles and Kendall Jenner had a dinner date and went in on disclosing some home truths.

Taking over from James Corden to play host on the Late Late Show , Harry invited his long-time pal Kendall to have a second swing at the show's “Spill Your Guts” feature, which sees contestants having to answer some invasive, all-revealing questions or eating some obscure delicacies like salmon smoothie or the I' m A Celeb -style animal genitalia.

Naturally, conversation quickly turned to the pair's pre-existing relationship with Kendall asking the question — as written by the show's producers — “Which songs on your last album were about me?”

Harry evidently did not see the question coming and hid his face in his manicured hands immediately, before tucking a napkin in his Gucci collar and gnawing down on some cod sperm. “What are we doing?” he laughed as he struggled with the forfeit.

Read More: We’ve Listened To Harry Styles’s ‘Fine Line’ Album And This Is What You Need To Know

Other awkward questions that saw the pair reaching for the plate and not giving the truth was Harry asking Kendall: “You're the highest paid supermodel in the world, who is the most unlikeable supermodel in the world?” Ever the professional, Kendall admitted that she has the answer but avoided sharing it and immediately sipped at her unpalatable salmon smoothie. Next, Kendall went on to ask Harry to rank the music of his One Direction peers’ solo efforts but the 25-year-old musician instead opted to chew down on a giant water scorpion.

With their tête-à-tête complete, the pair headed over to the Late Late Show sofa to be joined by Tracee Ellis-Ross to continue the question time. As host, Harry led the conversation and produced a photograph of Kendall in her teenage years holding a One Direction sign and demanded context on the photograph, with the 23-year-old model admitting that she had been “asked” to make the sign, rather than having made it off her own back as a serious Directioner. Okay Kendall, if you insist.

More from British Vogue...

Harry Styles and Kendall Jenner Are “Leaning on Each Other” After Splitting from Their Partners

The supermodel’s attendance at one of Styles’s recent concerts has some fans raising eyebrows.

Exes Harry Styles and Kendall Jenner are finding comfort in each other after each split from their significant other this past month.

Styles is reportedly on a break from his relationship with Olivia Wilde , whom he had been dating for the past two years since being cast in her psychological thriller, Don't Worry Darling . Meanwhile, multiple outlets recently reported that Jenner and her NBA star boyfriend of two years, Devin Booker , have broken up for a second time.

Now, it seems that Styles and Jenner, who have been romantically linked on multiple occasions starting in 2013, may have rekindled their connection amid their breakups.

"Harry and Kendall have always stayed in touch, but in light of their recent splits, they have more time for one another," an insider told The Sun . " And Harry has had Kendall's ear over his break-up with Olivia. Kendall is one of the few people to understand the level of fame and scrutiny which Harry endures. She is also dealing with her own tough time."

The Sun also noted that the two have been "leaning on each other" in the past few weeks.

The former flames have maintained a friendship long after their romance ended. Back in 2019, Jenner even made a guest appearance on The Late Late Show when Styles filled in for host James Corden.

Fans have been speculating about the former couple since Jenner attended one of Styles's Los Angeles concerts earlier this month. Video footage captured the model dancing alongside friend Hailey Bieber and sister Kylie Jenner, and one viral TikTok even alleged that the singer blew a kiss to Jenner during his song "Love of My Life" (which many believe is about her).

Still, The Sun 's source added that their renewed post-breakup connection may just be platonic.

"Close as they are, Harry and Kendall found dating difficult, and all of those practical problems they faced years ago are still there," the source continued. "That said, their friends speculate that they might hang out over the holidays. In the past they have gone away together shortly after respective break-ups, so they could very well end up on a yacht soaking up the sun in the next couple of months."

As an associate editor at HarpersBAZAAR.com, Chelsey keeps a finger on the pulse on all things celeb news. She also writes on social movements, connecting with activists leading the fight on workers' rights, climate justice, and more. Offline, she’s probably spending too much time on TikTok, rewatching Emma (the 2020 version, of course), or buying yet another corset. 

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Kendall jenner & harry styles -- all hands on deck (photos), kendall jenner & harry styles all hands on deck.

Kendall Jenner and Harry Styles became extra familiar with each other on a luxury yacht in St. Barts.

The two were spotted Wednesday getting handsy after reports surfaced they'd been vacationing together in Anguilla the night before.

It's unclear if the two are "officially official" but judging by the pics, the 20-year-old supermodel and 21-year old pop star certainly have no problem packing on the PDA.

Anchor's aweigh.

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Harry Styles and Kendall Jenner Share a Sweet Moment Inside the 2019 Met Gala

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Amid the fairytale princess gowns, chandeliers and sparkles of the  2019 Metropolitan Museum of Art's Costume Institute Gala , a true moment appeared to unfold between Kendall Jenner and Harry Styles.

In an adorable photo taken inside the star-studded event, Jenner beamed out a giant smile while being reunited with the One Direction heartthrob, who was serving as co-chair of this year's gala.

Styles, 25, looked just as thrilled to see the model and reality star in her orange feathered gown, grinning and placing his hand on her waist as the two caught up.

Jenner, 23, was attending the event with her famous family, including sister Kylie , who also wore a feather ensemble, while Styles rocked a sheer black Gucci top, high-waisted pants and a pearl teardop earring.

The pair have sparked dating rumors on and off since 2013, when they were spotted driving away together after a visit to West Hollywood hot spot, Craig’s.

In 2015, they were snapped getting cozy on a yacht during a sun-filled vacation in St. Barts, and the following year a source described the pair as being “super touchy feely ” during a lunch date in Los Angeles.

Following the lunch, another source said there was nothing romantic going on between the pair. “Nothing was ever going on with them. They hang out a lot,” the source said.

Jenner was also seen cheering on Styles at the final show of his Harry Styles: Live on Tour world trek in Inglewood, California, last June.

Whether or not the two have ever embarked on romance, they sure look good together! See the latest on cute couples who attended the 2019 Met Gala below.

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SS Daley Launches Womenswear—Watched By Harry Styles in the Front Row

By Alice Newbold

Stuart C. Wilson/Getty Images

Steven Stokey-Daley in his studio.

In the lead up to  London Fashion Week , SS Daley’s spring 2025 show swiftly became the most hyped presentation of the season.  Harry Styles  would be on the front row!  Cate Blanchett  his seatmate! Rumours around the designer’s debut womenswear outing swirled. “I can neither confirm nor deny,” said Steven Stokey-Daley with a glint in his eye, just days out from his schedule slot.

In the end, the whispers proved to be true (although it was Emma Corrin, rather than Cate Blanchett, repping the thespians on the day). Styles , who bought a  minority stake  in the delightfully eccentric British label in January, watched as his bespectacled Liverpudlian friend sent his first solely female edit out into the hallowed halls of the Royal Academy, where just 100 industry faces were invited to join him.

Harry, delicious as ever in SS Daley’s  Brideshead -with-a-twist separates and (well-worn) Vans, must have been feeling chipper about his investment, as the collection played out with all the hallmarks–sweet animal-print knits, crisp yet nostalgic high-waisted suiting–that put the beloved young brand on the map, but with the newness required to attract a fresh audience. “Half of it is a very clear overlap with the men’s [line], the other is a complete new exploration and development of ideas for the customer who wants more of their wardrobe to be from us,” says Stokey-Daley, noting that loyalists have often probed him regarding what, exactly, an SS Daley dress might look like.

The answer is a craft-driven exploration of the point where the codes of mens- and womenswear overlap. Think: strict tailoring meets splashy florals, starched shirting teamed with ceramic jewellery, and tuxedo bib pleats found on gathered dresses. Inspired by the British artist Gluck – who was born in 1895 as Hannah Gluckstein, but rejected gender pronouns and also went by the names Peter and Hig–Stokey-Daley became enchanted by the painter’s universe and the individuals who moved within it, such as the florist Constance Spry and journalist Edith Shackleton Heald.

Before Gluck’s death in 1978, the creative donated some 70 garments belonging to past lovers—and just one piece of their own androgynous uniform–to the Brighton Museum. These, along with Gluck’s paintings of flowers arranged by Spry, and the quintessential doilies and tablecloths found in tea rooms (Gluck was a descendant of the Lyons family), formed the basis of Stokey-Daley’s latest work. His colourful, abstract suits and painstakingly beaded tops are, in fact, Gluck’s signature bouquets blown up to look like pixelated cross-stitch patterns, while the dog-printed silk blouses were born from a picture donated by one of the archivists Stokey-Daley befriended for the project. How could he say no to a Dalmatian? “We always have points of humour and levity and so, it’s a take on this,” he explains of infusing functional pieces with charm, individuality and, yes, pets.

It is the outerwear that the designer is most proud of, particularly the broadcloth trench coat belted over a white ruched shirt and feathered tie, and an organza slip with sunray pleats edged in black organza, which moves like water. “There are no bells and whistles,” he explains of stripping back his usual theatrics to focus on the work. “I really want this to just be about this.”

Describing himself as a “slow and steady wins the race type of person”, he thought long and hard about the decision to unveil womenswear now. “I think in this moment, London is about to show that it’s resilient,” shares the twenty-something still at the start of his career. “Forward motion and creativity and new ideas prevail–we have to think like that, otherwise I get a bit depressed.” With rapturous applause–and this season’s Queen Elizabeth II Award also under his belt–there is nothing to feel glum about in Steven Stokey-Daley’s world. Even Harry Styles says so.

This article was originally published on Vogue.com . 

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Never Forget Harry Styles and Kendall Jenner's PDA-Filled Yacht Vacation

There's a reason why kendall jenner and harry styles' joint appearance on the late late show went so swimmingly..

There's a reason why  Kendall Jenner and Harry Styles ' joint appearance on  The Late Late Show went so swimmingly. 

The singer filled in for  James Corden as a guest host on Tuesday's episode, during which he and the  Keeping Up With the Kardashians  star played Spill Your Guts or Fill Your Guts . During the segment, Kendall agreed to rank her siblings according to their parenting skills, while Harry opted to consume cod sperm  rather than answer her question of which songs on his last album are about her.

Kendall, 24, and Harry, 25, go way back and have occasionally sparked dating rumors on and off since 2013. Over the New Year's holiday in 2016, the two got cozy on a luxury yacht while vacationing together  in St. Barts. The two were also joined by Ellen DeGeneres  and wife  Portia De Rossi .

"Why are they a good match? Well, they're both super hot, super great, sweet people," Kendall's sister Khloe Kardashian later told E! News . "And if I'm on a yacht in St. Barts if I'm—how old is she, 20? He's 20?—hey, I ain't mad at you, Kenny. Do your thing, girl!"

See photos from Kendall and Harry's Caribbean vacation:

The two show some PDA a yacht in St. Barts.

The two enjoy some R&R.

Kendall stunned in a white bikini.

The two gaze at the sea.

The  One Direction singer grabs the reality star's foot playfully.

The reality star climbs aboard, with little help from the singer...

The reality star shows off her trim figure in a crimson two-piece.

The reality star adjusts her bikini top.

The reality star covers up in the wind.

Ellen DeGeneres & Portia De Rossi join the reality star and  One Direction singer, who have sparked romance rumors for two years, for lunch on a yacht in St. Barts on New Year's Day.

Weeks later, Kendall and Harry attended a private party  at the Troubadour rock club in West Hollywood with her mother Kris Jenner . The two appeared to cool things off for a few months. In April 2016, a source told E! News that they were "hanging out again," but were not "officially dating."

In January 2018, Kendall attended Harry's concert in Los Angeles with friends and was spotted dancing and giving him a standing ovation .

This past May, the two rumored exes were all smiles as they  reunited at the 2019 Met Gala .

Watch  Keeping Up With the Kardashians on Sundays at 9/8c only on E!

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Harry Styles, 27, shows off his toned physique as he cosies up to girlfriend Olivia Wilde, 37, while enjoying yacht trip during romantic getaway to Italy

By Lydia Spencer-elliott For Mailonline

Published: 15:21 EDT, 9 July 2021 | Updated: 03:44 EDT, 10 July 2021

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They haven't been able to keep their hands off each other as they've soaked up the summer sun. 

And Harry Styles , 27, and Olivia Wilde , 37, looked more loved up than ever as they cosied up in the sea while enjoying a trip on a yacht in Italy on Friday. 

The Fine Line hitmaker showed off his toned tattooed physique as he dried himself off with a towel after taking a dip in the sea with his girlfriend by Giglio Island. 

Fun in the sun: Harry Styles, 27, and Olivia Wilde, 37, looked more loved up than ever as they cosied up in the sea while enjoying a trip on a yacht in Italy on Friday

Muscles: The Fine Line hitmaker showed off his toned tattooed physique as he dried himself off with a towel after taking a dip in the sea with his girlfriend by Giglio Island

Meanwhile, Olivia showcased her incredible figure as she soaked up the rays on the vessel.

Taking some much-needed time to relax, the film director looked content as she sunbathed and read her book. 

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But Harry couldn't help but shower her with affection as he poked his face under her novel to give her a kiss. 

It's no surprise that Harry was lavishing Olivia with attention as she looked effortlessly chic aboard the yacht. 

Inseparable: Taking some much-needed time to relax, the film director looked content as she sunbathed and read her book with Harry close by to steal a kiss 

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The Booksmart director opted for a high-waisted two-pice, which she kept simple and styled with a pair of stylish black sunglasses. 

She pushed her caramel tresses back and away from her face in a stylish slicked back look as she kept hydrated in the sun.   

Olivia showcased her natural beauty and appeared to go makeup free for the day of swimming and snorkelling while Harry showered off. 

Holiday Harry: The singer proved he'd been putting the time in at the gym as he flaunted his incredible physique on the back of the boat

Stylish: It's no surprise that Harry was lavishing Olivia with attention as she looked effortlessly chic aboard the yacht

Effortless: Olivia showcased her natural beauty and appeared to go makeup free for the day of swimming and snorkelling while Harry showered off 

It wasn't long before Harry was convincing Olivia to join him in the water for a romantic swim together. 

Harry had been keeping this casual in a forest green T-shirt and a blue cap, which he quickly removed for a swim after puckering up on deck. 

The One Direction star joyfully launched himself into the ocean without hesitation and held his nose as he went. 

Olivia smiled as she watched her boyfriend bomb into the sea, before joining him in the water to snorkel.  

Come on! It wasn't long before Harry was convincing Olivia to join him in the water for a romantic swim together

Laidback look: Harry had been keeping this casual in a forest green T-shirt and a blue cap, which he quickly removed for a swim after puckering up on deck

See ya: The One Direction star joyfully launched himself into the ocean without hesitation and held his nose as he went

Off he goes: Olivia smiled as she watched her boyfriend bomb into the sea, before joining him in the water to snorkel

In the water together, the couple kept an eye out for marine life as they donned goggled and snorkels. 

Harry rubbed his eyes as he got used to the salt with Olivia following closely behind.  

The star re-adjusted his goggle as he went, making sure for the best visibility to investigate the Italian waters. 

The couple seemed content as they paddled along together in the shimmering water before taking a break on some nearby rocks.  

Expedition: In the water together, the couple kept an eye out for marine life as they donned goggled and snorkels

Paddle: Harry rubbed his eyes as he got used to the salt with Olivia following closely behind

Swim: The couple seemed content as they paddled along together in the shimmering water before taking a break on some nearby rocks

Taking a breather in the shallow water, Harry and Olivia couldn't held but put on a PDA display as they shared a kiss with their snorkels. 

Visible from behind, Olivia was wearing a gold cross necklace, which Harry wore in his Lights Up video and gifted to her. 

The singer passionately wrapped his arms around his girlfriend as they embraced for a steamy kiss in the sea. 

The pair were clearly enjoying each other's company as they happily chatted in the sunshine before setting off for another couple of lengths. 

Beaming from ear to ear, Olivia nestled up to Harry at the picturesque beach spot.  

Rest stop: Taking a breather in the shallow water, Harry and Olivia couldn't held but put on a PDA display as they shared a kiss with their snorkels

Romantic: The singer passionately wrapped his arms around his girlfriend as they embraced for a steamy kiss in the sea

Happy couple: The pair were clearly enjoying each other's company as they happily chatted in the sunshine before setting off for another couple of lengths

Over the moon: Beaming from ear to ear, Olivia nestled up to Harry at the picturesque beach spot

Harry couldn't wait to get back to the snorkelling as he pulled on his mask like a pro.

The in-shape singer's impressive physique was on full display as he got ready for round two of sea life spotting. 

Once prepared, he pushed off a nearby rock and got back to his underwater activity.  

Back at it: Harry couldn't wait to get back to the snorkelling as he pulled on his mask like a pro

Let's go: Once prepared, he pushed off a nearby rock and got back to his underwater activity.

Meanwhile, Olivia showcased her taut abs as she pulled herself back onto the yacht after her dip in the sea. 

The film director effortlessly pulled herself onto the boat as Harry clambered behind her. 

Olivia lay down in the sun and washed as Harry washed the salt water off his body with a shower head. 

Harry's back muscles rippled as he reached round to get every inch of his tanned torso clean. 

Toned: Meanwhile, Olivia showcased her taut abs as she pulled herself back onto the yacht after her dip in the sea

Following in her footsteps: The film director effortlessly pulled herself onto the boat as Harry clambered behind her

Squeaky clean: Olivia lay down in the sun and washed as Harry washed the salt water off his body with a shower head 

Dry again, Harry put his blue cap back on and added a pair of effortlessly cool shades. 

While Olivia returned to her book, Harry found some entertainment of his own and started snapping pictures with his vintage camera.  

Harry has been spotted out and about on the yacht several times this week as he enjoys some time off from his successful solo music career. 

He and Olivia were first linked as a couple while working together on her latest film Don't Worry, Darling last year. 

Shower time: Harry's back muscles rippled as he reached round to get every inch of his tanned torso clean

Olivia pouted as she watched Harry in the shower before handing her beau a fresh towel to dry off. 

Harry proved he'd been putting the time in at the gym as he flaunted his incredible physique on the back of the boat. 

Harry rubbed his wet chestnut tresses in the towel as his wet shorts gave a flash of his thigh 

Post swim: Olivia pouted as she watched Harry in the shower before handing her beau a fresh towel to dry off

Harry and Olivia have jetted for a romantic getaway in Italy following the wrap of his latest movie, LBGTQ drama, My Policeman, which he had been filming in London over the past few months.

During his time in the UK, he was kept company by his other half. 

A source said that they were 'having an awesome time,' seen 'going on walks outside in the park and not hiding their relationship,' while 'grow[ing] even closer as a couple.' 

Getting dry: Harry rubbed his wet chestnut tresses in the towel as his wet shorts gave a flash of his thigh 

Summer style: Dry again, Harry put his blue cap back on and added a pair of effortlessly cool shade

'Yesterday, they enjoyed lunch outside and looked incredibly cute together,' the Entertainment Tonight insider said 

'They were both in a great mood and left the restaurant holding hands. Harry put his arm around Olivia as they walked back to her house.'

Her estranged husband, Jason Sudeikis, was also in London working on season two of his award-winning Apple TV plus series, Ted Lasso, which debuts in July.

And while the former couple work on a co-parenting routine for their two children, sources told Page Six that Jason is still 'heartbroken' over the end of their relationship.

Break: Harry has been spotted out and about on the yacht several times this week as he enjoys some time off from his successful solo music career

Creative: While Olivia returned to her book, Harry found some entertainment of his own and started snapping pictures with his vintage camera

Share or comment on this article: Harry Styles shows off his toned physique as he and girlfriend Olivia Wilde enjoy a trip on a yacht

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