In a revealing interview from the past, singer Harry Styles shared his preference for dating older women, specifically mentioning Angelina Jolie, Kate Moss, and Kate Winslet. Styles tantalized listeners by discussing his ideal girlfriend’s fashion choices. With his charismatic persona and daring fashion sense, the enigmatic star continues to intrigue fans, leaving them eagerly awaiting his next moves in both music and romance.
The ‘Watermelon Sugar’ singer revealed some personal information in an interview with Metro UK, including the fact that he is not great with words but understands what he wants his women to wear. He said, “I’m not really a pick-up line guy – I don’t know what I do. I like my girlfriends to wear black lingerie… definitely.”
During the same interview, when asked which older women he would date, Harry Styles said Angelina Jolie, Kate Moss, and Kate Winslet, excluding Madonna and Kylie Minogue from the list. He adds, “Sorry – it’s a no on Madonna and Kylie.” The singer said that he would have to turn down pop superstar Kylie Minogue if all the ladies in the world were at his feet. Kate Moss dated Johnny Depp, while Angelina Jolie was married to Brad Pitt.
Before his fame, Styles dated Felicity Skinner, whom he met via a mutual acquaintance. Despite living in various locations, the couple stayed together. After a year together, though, the two broke up. When Styles launched Caroline Flack in 2011, it was all over the press. In 2012, the couple ended their relationship, saying it was amicable. Flack was 14 years elder than Styles, who was just 18 at the time.
Several models, including Emma Ostill, Kendall Jenner, and Camille Rowe, were briefly associated with the singer. In addition, he was said to be seeing famous singer Taylor Swift as well.
After dating for almost 2 years, Olivia Wilde and Harry Styles broke up. The director (then 38) and the singer (then 28) initially met in September 2020 while filming ‘Don’t Worry Darling’, and by January 2021 they were attending a wedding as a couple. In January 2021, photos of the ‘Life Itself’ actress and the former ‘X-Factor hopeful’ holding hands at the wedding of Styles’ agent in Montecito, California, sent the internet into a frenzy.
Later in March 2023, Styles and Emily Ratajkowski were sighted kissing in Tokyo. Ratajkowski was seen with a pink and black jacket and a long black skirt, while Styles wore a white shirt with a black jacket and matching pants. The rumors about Styles dating Ratajkowski began following his breakup with Olivia Wilde at the end of last year.
Numerous sightings of Styles and Russell together in public have led some to speculate that the two are romantically involved. Photos of the two were posted to TikTok by user @ellahodgkinson in June, showing them out on a casual stroll in London.
