Harry Styles has been a focal point of public attention since his debut in 2010, attracting fans with both his music and personal life.
His relationships have often drawn curiosity, especially with names like Kendall Jenner, Taylor Swift, and Georgia Fowler making headlines.
While recent rumors suggest he may have started a new romance following his split from Taylor Russell, Styles has yet to provide confirmation.
Harry Styles attracts audiences with his music and romantic escapades (@harrystyles/Instagram)
Let’s revisit Harry Styles’ dating journey, tracing his relationships from his time in One Direction to the present day and exploring the speculation about his love life.
Harry Styles’ Girlfriend Timeline: From 2011 to the Present
Caroline Flack: 2011
Harry was linked to Caroline Flack, a judge on The X Factor, shortly after his appearance on the show. Their 14-year age difference sparked considerable media attention. Caroline later shared in her autobiography that Harry had openly expressed his admiration for her.
Tragically, Caroline passed away in 2020. Harry honored her memory by wearing a black ribbon at the Brit Awards and a badge reading “Treat People With Kindness” during his performance.
Taylor Swift: 2012
When Harry and Taylor Swift were seen spending time together, fans were thrilled by this pairing of two musical powerhouses. Though their relationship was brief, its impact resonated through the songs they both wrote afterward, cementing their time together in pop culture history.
Kendall Jenner: 2013
Harry’s next rumored relationship was with model and reality TV star Kendall Jenner. While the two remained private, reports of their connection circulated widely.
Nadine Leopold: 2015
Following his time with Kendall, Harry was romantically linked to Austrian model Nadine Leopold. Though the pair never confirmed their relationship, they were spotted together multiple times, fueling speculation about their involvement.
Georgia Fowler: 2015
Georgia Fowler, a model from New Zealand, was rumored to be the inspiration for Harry’s song Kiwi, released in 2017. Although there was no solid evidence of a romantic connection, fans often speculated based on a YouTube video featuring Georgia.
Kendall Jenner Again: 2016
After reportedly parting ways in 2013, Harry and Kendall reignited rumors of a romance after attending a New Year’s Eve party together. The speculation continued after the 2019 Met Gala, but they have consistently maintained a close friendship.
Remembering Harry’s connection with Caroline Flack despite his evolving romances (@carolineflack/Instagram)
Tess Ward: 2017
Food blogger Tess Ward was reportedly linked to Harry in 2017. However, their rumored relationship ended when Tess reconciled with her ex-boyfriend.
Camille Rowe: 2018
French model Camille Rowe was one of Harry’s more publicly acknowledged relationships. They dated for about a year before breaking up.
Harry later confirmed that his song Cherry reflected his feelings during their time together, highlighting the challenges and emotions of their relationship.
Olivia Wilde: 2021
Harry met Olivia Wilde on the set of Don’t Worry, Darling, which began filming in late 2020. Their romance became public in January 2021 when photos of them holding hands at a wedding surfaced.
Olivia later praised Harry for his work on the film, commending his humility and talent. Their relationship included memorable moments like a romantic boat outing, but it eventually came to an end.
Taylor Russell: 2023-2024
Harry’s relationship with actress Taylor Russell was marked by low-key appearances, starting with a date in London during the summer of 2023. Though they appeared close at public events, their relationship reportedly ended in 2024 after a challenging period.
Current Speculations
Harry Styles has recently been linked to singer Olivia Dean. They’ve been seen together at events like a London burger joint and a music festival in Spain. While some speculate about a romantic connection, others believe their relationship might be platonic or collaborative.
An insider shared that Harry enjoyed his time with Olivia at the festival, adding fuel to the speculation about their potential relationship. However, no official confirmation has been made.
