Harry Styles’ love of a mature woman – and their love of his style – is evident from his dating history in the last decade, as news of his new relationship has been revealed.
The former One Direction singer, 31, is understood to be in the early stages of dating Zoe Kravitz, 36, and the pair have been spotted together on a date.
Zoe, who is five years older than the hitmaker, was ‘spotted kissing him at a London restaurant’ just days before they were sighted together in Rome.
While their romance continues to blossom, the slight age gap will come as no surprise to Harry’s loyal fans.
The star has mostly dated older women for the past decade, pursing ladies who in turn often end up stealing his hipster style.
Previously speaking about his ‘type’, Harry said: ‘I love a bit of cheek, and I don’t like girls to look the same as other girls.’
How Harry Styles’, 31, (left, in 2022) string of older lovers have taken inspiration from his quirky wardrobe – as his romance with Zoe Kravitz, 36, is revealed (right, this month)
Zoe, who is five years older than the hitmaker, was ‘spotted kissing him at a London restaurant’ just days before they were sighted together in Rome
Harry added that he doesn’t have a preference between blondes and brunettes.
‘I wouldn’t not go out with a girl because of her hair colour,’ he said magnanimously. As for what he doesn’t like, he said: ‘A bad attitude, like when they are rude…’
In 2011, when he was just 17 years old, Harry began dating late presenter Caroline Flack, who was already in her 30s.
While it soon fizzled out, the following year he had a ‘short-lived thing’ with actress Emily Atack, who was 22.
The Rivals star said near the time how it was ‘just a bit of fun’ and they ‘both went off in our opposite directions’.
Harry’s love for an older woman became very apparent when he was linked to Pussycat Doll Nicole Scherzinger in 2013, when she was 35 and he was just 19.
The Watermelon Sugar star was also linked to American actress Erin Foster, after reportedly being introduced by his former fling Kimberly Stewart – both of whom are 12 years his senior.
Harry’s other brief romances include Kiko Mizuhara, 34, Camille Rowe, 35, Tess Ward, 35, Georgia Fowler, 33, Sara Sampaio, 35, and Kendall Jenner, 29.
Harry and ex Olivia Wilde paired ripped denim jeans with white tops for one outing together, with Harry wearing a Beastie Boys band T-shirt (pictured in 2021)
It wasn’t the first time they coordinated their looks, as they donned matching white hoodies while posing with their castmates on the set of their movie Don’t Worry Darling in Los Angeles
Despite his prominent age gap relationships, Harry’s influence on his mature lovers is clear to see, with some ladies being snapped stealing his style.
Harry has never been shy when it comes to using fashion to express himself and is often seen wearing, gender-fluid and quirky styles.
He’s often stepped out in bold colours and flamboyant patterns as he pushes the boundaries on traditional menswear.
In 2021, during a romantic trip to Italy, Harry and his ex Olivia Wilde packed on the PDA as they sported matching looks.
The actress, who is 10 years older than him, paired ripped denim jeans with white tops for the occasion, with Harry wearing a Beastie Boys band T-shirt.
It wasn’t the first time they coordinated their looks, as they donned matching white hoodies while posing with their castmates on the set of their movie Don’t Worry Darling in Los Angeles.
In an image shared on Instagram by cast member Asif Ali, Harry and Olivia – who split in 2022 – were seen smiling broadly as they stood with their arms around one another.
Kendall Jenner, who dated him in on and off between 2013 and 2016, also took inspiration from his looks, having recreated outfits such as a v-neck white top paired with skin-tight black trousers.
Another borrowed look by the model was a casual flannel outfit paired with a crop top and black leggings. Harry had worn a white top with his outfit and skinny jeans.
Kendall Jenner, who dated Harry on and off between 2013 and 2016, also took inspiration from his looks, having recreated outfits from the star
Another borrowed look by the model was a casual flannel outfit paired with a crop top and black leggings. Harry had worn a white top with his outfit and skinny jeans
In 2014, Harry and Erin Foster both rocked a denim look together as they enjoyed a date picking pumpkins.
Tess Ward completely copied and pasted Harry’s look in 2017 when she attended the Audio Polo Challenge.
She wore a floral red and white blouse under a black blazer, pairing the look with black trousers.
The pattern and colour was identical to Harry’s Gucci pattern shirt that he was pictured wearing before, with the same accessories.
Model Georgia Fowler also took inspiration from Styles, appearing at a Tommy Hilfiger fashion show in 2024 in a bright double denim outfit.
It was a similar, but less sparkly look that Harry wore when he before in a darker version for the Jingle Bell Ball in 2019.
History appears to be repeating itself, with Zoe Kravitz already stealing her new man’s look.
She gave a nod to her new beau as she emerged in New York on Tuesday for the first time since their new romance came to light.
Stepping out for promo duties ahead of the NYC premiere of her new movie Caught Stealing on Thursday, Zoe stole Harry’s style, rocking a black suit and white shirt with an oversized collar – the spitting image of a Gucci look Harry famously rocked in 2022.
Tess Ward completely copied and pasted Harry’s look in 2017 when she attended the Audio Polo Challenge after they were linked that year
Harry pictured in 2014 with his older ex Erin Foster as the pair rocked a denim look while picking out pumpkins together
Model Georgia Fowler also took inspiration from Styles, appearing at a Tommy Hilfiger fashion show in 2024 in a bright double denim outfit
Zoe looked relaxed in her achingly cool ensemble, adding shades and clutching a coffee as she headed into the CBS studios.
Sources close to Harry suggest Zoe might finally be the woman he settles down with after a decade of dating.
‘Zoe is just Harry’s type,’ said one friend. ‘She’s cool, edgy and really, really interesting.
‘He likes a woman he can have a chat with, he likes to go a bit deep, and Zoe is extremely clever and successful. Like him, she is very much into her work and is ambitious. They are well matched and apparently get on very, very well.’
While Olivia Wilde is Harry’s last long-term relationship, he has dated Emily Ratajkowski, Taylor Russell and Olivia Dean over the past three years.
In June of this year, Harry was pictured kissing producer Ella Kenny at Glastonbury Festival.
However, a source played down the snog, telling The Sun: ‘Harry and Ella had fun together at Glastonbury and shared a kiss on the dance floor. They had a good time in the moment but it doesn’t mean it will evolve into anything.’
Harry has never been shy when it comes to using fashion to express himself and is often seen wearing, gender-fluid and quirky style (pictured in 2023)
