Caroline Flack: 2011
Harry and X-Factor judge Caroline Flack were linked shortly after the singer competed in the UK talent show. They immediately faced intense media scrutiny for their age gap (Harry was 17 while Flack was 31 at the time), but they still appeared to give things a go.
Writing of Harry in a later autobiography, Caroline revealed: "I already knew that he had a crush on me, he’d made it pretty obvious."
Tragically, Caroline passed away in February 2020. Harry paid tribute to the late star by wearing a black ribbon to the Brit Awards that year. When he took to the stage to perform, he also wore a badge reading: "Treat people with kindness."
Taylor Swift: 2012
Music fans understandably lost the plot when pictures surfaced of Harry and Taylor Swift going on dates and hanging out together. Their relationship was something of a celebrity couple enigma—both were peaking in their careers (though you could say they never stopped). Brad and Jen, eat your heart out.
While the relationship reportedly lasted mere months, the legacy lives on in the songs they both went on to write about each other.
Kendall Jenner: 2013
Next on Harry's A-list romance repertoire was reality star and a then up-and-coming model, Kendall Jenner.
The half sister of the infamous Kardashian trio was—and has remained to be— incredibly private about her life behind the cameras. Getting a glimpse of them together was tough to come by, but at the time, reports about their relationship were rife.
Nadina Leopold: 2015
Things with Kendall apparently didn't last long. He was later linked to Austrian model Nadine Leopold. Neither ever confirmed their romance, but multiple sightings of them together throughout 2014 and 2015 led many to believe they were the real deal at one point.
Georgia Fowler: 2015
Of course, we can't forget Fowler-gate, or perhaps more accurately Kiwi-gate. The New Zealand model was long believed to be the muse behind Harry's hit song Kiwi, which was later released in 2017 after they were linked.
There was no actual evidence of the pair being anything more than friends, just a suss YouTube video from Georgia and probably a whole bunch of fanfic.
Kendall Jenner... again: 2016
After reportedly splitting two years prior, Kendall and Harry rekindled things after a New Years Eve party, according to Page Six.
There were also reports they rekindled things again after the 2019 Met Gala. Whatever the confirmed truth, the pair are clearly good friends, they just couldn't seem to hang out without sparking a million dating rumours.
Tess Ward: 2017
Keeping up? Harry was rumoured to be dating food blogger Tess Ward in 2017, but apparently broke up when Tess decided she still had feelings for her ex, per Cosmopolitan.
Camille Rowe: 2018
French model Camille Rowe was linked to Harry in 2017, but this relationship hit different because it was publicly acknowledged by Harry himself.
They dated around a year before parting ways, and Harry confirmed that his song Cherry was about Camille.
The song references the tougher realities of their relationship: "I wanted it to reflect how I felt then. I was feeling not great," Harry explained.
"It’s all about being not great. Because you get petty when things don’t go the way you want it. There’s parts that’s so pathetic.”
Olivia Wilde: 2021
Olivia and Harry got to know each other on the set of Olivia's film, Don't Worry, Darling, which began filming in late 2020.
Around the same time, Olivia split from her fiancee, Jason Sudeikis, with whom she shares two kids.
Then in January 2021, pictures of Harry and Olivia holding hands at a wedding surfaced, sending the internet into overdrive. At the time, PEOPLE claimed they had been dating "for a few weeks".
In February 2021, Wilde penned a tribute to Harry for his part in her female-led film, writing to Instagram: "Little known fact: most male actors don’t want to play supporting roles in female-led films. The industry has raised them to believe it lessens their power (i.e financial value) to accept these roles."
She then celebrated her rumoured boyfriend who starred alongside the formidable Florence Pugh: "Enter: @harrystyles, our 'Jack' . Not only did he relish the opportunity to allow for the brilliant @florencepugh to hold center stage as our 'Alice', but he infused every scene with a nuanced sense of humanity."
She continued: "He didn’t have to join our circus, but he jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards."
With reports continuing to colour their sweet relationship, and those pictures of a steamy makeout sesh on a boat in July, it looks like they're both going stronger than ever. Happy for ya, Harry!