Joshua Goldman
Joshua Goldman
min read · August 31, 2025 · Entertainment

Harry Styles' Love Affair with Style: How His Older Lovers Follow His Fashion Lead

Harry Styles ' love of a mature woman - and their love for his style - is evident from his dating history in the last decade, as news of his new relationship was revealed earlier this week.

HARRY STYLES' TYPE TAKES CENTER STAGE: THE ONCE-DIRECTION SINGER'S PATTERN OF DATING OLDER WOMEN EXPOSED

In a relationship that's heating up faster than his sold-out tour, Harry Styles has been spotted getting cozy with none other than the ravishing Zoe Kravitz. The 31-year-old heartthrob, known for his effortless charm and sartorial splendor, has made no secret of his fondness for older women - and it looks like he's found his perfect match in the stunning 36-year-old actress.

As we delve into Harry's dating history over the past decade, one thing becomes glaringly apparent: he's always been drawn to the mature and sophisticated. From his earliest fling with Caroline Flack back in 2011 (yes, that's right - at just 17!) to his more recent romances with Olivia Wilde, Emily Ratajkowski, and Taylor Russell, Harry has consistently sought out women who are not only stunning but also confident, independent, and unafraid to take a chance on love.

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

But it's not just their age that sets these women apart - it's their sense of style. And by that, we mean they're often spotted swiping Harry's looks, from his iconic Gucci ensembles to his more daring fashion experiments. Kendall Jenner, who dated him on and off between 2013 and 2016, was known for recreating outfits inspired by the singer - think ripped denim jeans paired with a white top, or a casual flannel outfit paired with black leggings.

And then there's Tess Ward, who went one step further in 2017 by copying Harry's exact look at the Audio Polo Challenge. We're talking identical patterned shirts, identical accessories... it was as if she'd taken a direct screenshot from Harry's wardrobe and reenacted it on stage.

So what is it about these women that sets them apart? Sources close to Harry suggest that they share a common trait - intelligence, ambition, and a sense of adventure. "Zoe is just Harry's type," says an insider. "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... Zoe is extremely clever and successful, like him."

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)

As for Zoe herself, she seems to be embracing her new role as Harry's leading lady in more ways than one. The actress was spotted wearing a striking black suit and white shirt with an oversized collar - eerily reminiscent of Harry's 2022 Gucci look - as she made her way into the CBS studios in New York this week.

And it looks like Zoe might just be the one to finally bring some stability to Harry's love life. Sources close to the couple suggest that they're getting along famously, with one insider revealing, "They are well matched and apparently get on very, very well."

Of course, we can't help but wonder what's next for this power couple - will they make their relationship Instagram-official? Or will they keep things under wraps for now? One thing's for sure: Harry Styles has finally found his perfect match in Zoe Kravitz. And it looks like she's not just stealing the spotlight... she's also stealing his style.

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 related news, we can't help but take a look at Harry's other romantic endeavors over the years - from his brief fling with Nicole Scherzinger (when he was just 19 and she was 35) to his more recent relationships with Olivia Dean and Ella Kenny. But it seems that Zoe Kravitz might just be the one who finally brings some lasting love into Harry's life.

As we wrap up this tale of love, style, and a dash of age-gap romance, one thing becomes clear: Harry Styles is not afraid to take risks in love - or in fashion. And if his past is any indication, he's about to find himself swept off his feet by someone who truly understands him.

THE SCHOLARLYNOTE.COM EXCLUSIVE GUIDE TO HARRY STYLES' DATING HISTORY

Harry's style has often been recreated, such as this casual number

  • 2011: Harry begins dating late presenter Caroline Flack (in her 30s) at just 17 years old. The romance is short-lived, but sets the stage for his future love life.
  • 2012: He's linked to actress Emily Atack (22), with whom he shares a "short-lived thing".
  • 2013: Harry sparks controversy when he begins dating Nicole Scherzinger (35) - at just 19 years old. The romance fizzles out, but leaves fans buzzing about their age gap.
  • 2014: He's spotted getting cozy with Erin Foster (12 years his senior), who later recreates one of his outfits on a date to pick pumpkins.
  • 2015-2016: Harry dates Kendall Jenner (29) on and off for several years, with the model frequently swiping his looks and outfit ideas.
  • 2017: Tess Ward is spotted copying Harry's exact look at the Audio Polo Challenge - down to the same patterned shirt and accessories!
  • 2019: Georgia Fowler recreates one of Harry's outfits (a bright double denim ensemble) at a Tommy Hilfiger fashion show in 2024.
  • 2021-2022: He's linked to Olivia Wilde (10 years his senior), with whom he shares a romantic trip to Italy and several PDA-filled moments on set.
  • 2023-present: Harry is spotted getting cozy with Zoe Kravitz (36) - the latest addition to his long line of mature loves.

Stay tuned for more updates from The ScholarlyNote.com as this love story continues to unfold!

Harry pictured in LA in 2014

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

Harry wore the double denim sparkly look for the Jingle Bell Ball in 2019

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)