Harry Styles has quite the A-list dating history! From Taylor Swift to Kendall Jenner, the English star has been in relationships with several female artists.
Here's everything we know about the What Makes You Beautiful crooner's dating life!
Harry Styles began dating Caroline Flack in 2001. At that time, the singer was just 17 years old, and Caroline was already in her 30s.
After facing criticism for their age gap, the two stars eventually parted ways.
“I already knew that he had a crush on me; he’d made it pretty obvious,” the X Factor presenter had penned in her autobiography, Storm in a C Cup.
For those unversed, Caroline died in February 2024, after struggling with mental health issues.
Harry Styles was in a relationship with Emily Atack back in 2012. The British actress never publicly discussed her romance with the singer.
“We had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions,” Emily told Reveal Magazine in 2014.
Harry Styles dated Taylor Swift for a year before the two stars called it quits in 2013.
Rumors of Harry and Taylor's relationship sparked when the Watermelon Sugar singer was seen wearing the same paper plane necklace that the Bad Blood songstress had worn on several occasions.
Recalling his relationship with Taylor, Harry once said that "Relationships are hard, at any age. And adding in that you don't really understand exactly how it works when you're 18, trying to navigate all that stuff didn't make it easier."
Following his split from Taylor Swift, Harry Styles began dating Kimberly Stewart. The As It Was crooner was just 19 when he was first spotted with a then-33-year-old TV enjoying a dinner.
"Kim and Harry looked like they were enjoying each other's company," an insider told People magazine at that time. "Age doesn't really matter in the Stewart family."
Harry Styles crossed paths with Kendall Jenner when he was spotted enjoying dinner with the reality star in LA.
The two were then spotted together on several dates. However, things didn't last long, and they have been friends ever since.
Harry Styles was also in a relationship with Australian model Nadine Leopold. The former pair was seen together in November 2014 for the first time.
However, Harry and Nadine's romance didn't last long, as they parted ways in March 2015.
Harry Styles and Olivia Wilde began dating in January 2021, when the singer was spotted getting cozy with the actress at a friend's wedding.
The two, who worked together on the 2022 film Don’t Worry Darling, decided to separate ways in November 2022 after nearly two years of dating.
After his breakup with Olivia, Harry moved on with model Emily Ratajkowski.
Rumors of Harry and Emily's relationship sparked when the two stars were seen kissing on a busy street in Tokyo in March 2023.
Harry Styles started dating Taylor Russell in June 2023, following her appearance at the pop star's Vienna concert.
The two stars confirmed their relationship in August 2023 when they were seen holding hands during a cozy night out in London.
Unfortunately, Harry and Taylor's romance did not last long, and they called it quits after a year of dating.
Now, speculations are swirling that Harry Styles is in a relationship with actress Zoë Kravitz.
Rumors of Harry and Zoe's relationship began surfaced in August 2025, after the former One Direction star was spotted walking arm in arm with the 36-year-old actress in Williamsburg, Brooklyn.
However, neither of the two officially confirmed their romance.
Harry Styles is enjoying his single life as he's not dating anyone rightnow.