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He's reportedly single again after splitting from his girlfriend of 14 months, Taylor Russell.
But Harry Styles appeared to have brushed off any post-breakup blues on Friday night, as he stepped out in Rome during his Italian getaway.
The singer, 30, looked relaxed as he left the restaurant Il Pagliaccio after enjoying a meal with a group of pals.
He looked handsome in his effortlessly stylish outfit, donning an oversized blue button-up shirt, left untucked over a pair of black trousers.
The One Direction star also sported a pair of black trainers and draped a jumper over his shoulders.
Harry Styles appeared to have brushed off any post-breakup blues on Friday night, as he stepped out in Rome during his Italian getaway
The singer, 30, looked relaxed as he left the restaurant Il Pagliaccio after enjoying a meal with a group of pals
He looked handsome in his effortlessly stylish outfit, donning an oversized blue button-up shirt, left untucked over a pair of black trousers
Harry was joined by fashion designer and creative director for Valentino, Alessandro Michele, who lives in Rome.
Alessandro, 51, complemented Harry in a matching shirt, which he teamed with beige trousers and leather loafers.
The two friends shared a warm embrace as they bid each other goodbye for the evening and headed home.
And eschewing the more luxury modes of travel typically used by the rich and famous, Harry then hopped onto a Lime bike.
The Watermelon Sugar hitmaker was snapped cycling back home on the rental bicycle.
His Italian trip comes after it was reported earlier this month that Harry is back on the market after splitting from girlfriend Taylor, 29, following a 'make or break' holiday.
The pop star and the Canadian actress were last seen in public riding bikes together during an appearance in Tokyo, Japan, in April.
As weeks passed without being sighted together, speculation began that the genetically-blessed couple had gone their separate ways.
The One Direction star also sported a pair of black trainers and draped a jumper over his shoulders
Harry was joined by fashion designer and creative director for Valentino, Alessandro Michele, who lives in Rome (pictured left)
Alessandro, 51, complemented Harry in a matching shirt, which he teamed with beige trousers and leather loafers
The two friends shared a warm embrace as they bid each other goodbye for the evening and headed home
And the break-up news unsurprisingly delighted Harry's legion of devoted fans, with his overwhelmingly female fanbase rejoicing on social media.
Earlier this month, Taylor appeared at the star-studded Met Gala in New York without Harry, who remained on the other side of the Atlantic in London.
Friends have since claimed the couple opted to end the relationship after spending time together in the far east.
A source told The Sun: 'Harry and Taylor have ended their relationship. They went through a rough patch after their trip to Japan and are taking some time apart.
'He’s been in America and she’s been in London. They made a lovely couple and it was obvious Taylor made Harry happy.
'Things have become strained recently though and they’ve taken some time out.'
The reported split comes after a 'besotted' Harry was said to be ready to start a family with the actress.
Speaking in March, a source told MailOnline: 'Harry feels as if he has lived ten lifetimes already, but one thing is certain – his 30s will be nothing like his 20s.
His Italian trip comes after it was reported earlier this month that Harry is back on the market after splitting from girlfriend Taylor, 29, following a 'make or break' holiday (Taylor pictured at Met Gala earlier this month)
As weeks passed without being sighted together, speculation began that the genetically-blessed couple had gone their separate ways
And the break-up news unsurprisingly delighted Harry's legion of devoted fans, with his overwhelmingly female fanbase rejoicing on social media
Friends have since claimed the couple opted to end the relationship after spending time together in the far east
The reported split comes after a 'besotted' Harry was said to be ready to start a family with the actress
'He has experienced all the fame anyone could ever want. He is now ready for the next chapter.
'He is in love with Taylor. He wants a family with her and this is the next phase of his life.'
Harry and Taylor were spotted together for the first time last June as they exited a museum in London and at one point, also reportedly, held hands, per TMZ.
When the two stars first crossed paths is still unclear, but both Harry and Taylor attended the 79th Venice International Film Festival last year in September 2022.
Harry was notably promoting film Don't Worry Darling, while Taylor celebrated the premiere of Bones And All.
The Grammy winner previously dated Olivia Wilde from January 2021 until their split the following year in November 2022.
At the time of the break up, a source told People, 'He's still touring and is now going abroad. She is focusing on her kids and her work in L.A. It's a very amicable decision,' adding that 'they're still very close friends'.
Harry has historically been linked with a string of A-list women from Taylor Swift to Kendall Jenner, Emily Ratajkowski, French model Camille Rowe, Olivia Wilde and, most recently, Taylor.
The Grammy winner previously dated Olivia Wilde from January 2021 until their split the following year in November 2022 (Olivia pictured last year)