Harry Styles and gay ‘love of his life’ Alessandro Michele spotted wearing matching outfits in Rome

Harry Styles and Alessandro Michele hugging and laughing at the Met Gala

Harry Styles has reportedly split from his girlfriend Taylor Russell after a year together, and what better way to get over a breakup than by travelling to Rome and enjoying some pasta with your bestie Alessandro Michele?

It would seem that the “Watermelon Sugar” has done just that, as he’s been repeatedly papped in La Città Eterna over the last few days, most recently while hanging out with his much-loved friend Alessandro Michele.

Fashion icon Michele, who is gay and who was recently appointed Valentino creative director, stepped out in Rome with Styles in what Vogue described as matching outfits – and we describe as extremely similar outfits, because we clearly don’t have their keen eye for fashion.

Vogue reports that the pair were both spotted in “casual fits” during a night out. Styles “wore a blue button-down, left open at the top and untucked” and “styled his shirt with a pair of black trousers”, while Michele “paired his shirt with a pair of khaki pants, cuffed once to show show off his mahogany, patent leather loafers.”

Who is Alessandro Michele?

Fashion Designer Alessandro Michele (Getty)

Alessandro Michele has been described as “one of the loves of (Harry’s) life” by Grazia. He recently left Gucci and took over as artistic lead at Valentino following the departure of Pierpaolo Piccioli, who previously held the top job for seven years, and who had worked for the fashion giant for 25 years.

Michele is openly gay and lives in Rome with his longtime partner, professor of urban planning, Giovanni Attili.

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Alessandro Michele is credited with helping Harry Styles perfect his iconic “glam rock star look”. The pair also launched a collection called “HA HA HA” – their initials – a collection of dandy suits and bohemian silhouettes.

Grazia suggested that the matching outfits in Rome might be the “soft launch of a deeper relationship” between the two, but other than that, there’s little to suggest they’re more than just very good friends.

In a 2022 interview, Michele said: “Harry has an incredible sense of fashion… I came to understand that the styling of a look is a generator of differences and of powers, as are his reactions to the designs I have created for him, which he has always made his own; these reactions restore me with a rush of freedom every time.”  

Harry Styles relationships

Don't Worry Darling starring Florence Pugh and Harry Styles
Don’t Worry Darling starring Florence Pugh and Harry Styles. (Warner Bros.)

The former One Direction star and LGBTQ+ ally, who has always refused to comment on or confirm his sexuality, has dated some of the world’s most famous and successful women over the years.

The first of his relationships is believed to be with Love Island presenter Caroline Flack in 2011, when he was just 17 years old and she was already in her 30s. Caroline tragically died by suicide in February 2020.

After that, Styles dated Emily Atack in 2012. “We had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions,” the Inbetweeners star told Reveal Magazine (via Hello!) in 2014.

He then got together with none other than Taylor Swift, who he dated for a year before they broke up in 2013. Fans believe that Taylor Swift’s song “…Ready For It” is about Styles, others think his song “Two Ghosts” is about her.

Following Swift, it’s thought he had a fling with Pussycat Dolls singer Nicole Scherzinger. Styles “had a dalliance at the end of the X Factor in 2013 and met up again early last year,” a source told The Sun in 2015.

As if Styles was trying to complete a bingo card of the most famous women he could think of, he then went on to date Kendall Jenner. However, the pair are said to have split shortly after they started seeing each other in February 2014, according to Seventeen.

Kendall Jenner (James Devaney/GC Images)

He then dated a string of models including Nadine Leopold, Sara Sampaio and Georgia Fowler before getting back together with Kendall Jenner again, but it’s thought they broke up in 2017.

Harry Styles then dated Victoria’s Secret model Camille Rowe for a year; they split in 2018.

Fast forward to 2021, and his fans were very surprised when he was papped holding hands with actress Olivia Wilde at a friend’s wedding in January of that year. During that time the pair also worked together on the 2022 film Don’t Worry Darling, which Wilde directed and Styles starred in.

Olivia Wilde
Olivia Wilde. (Getty Images for MAKERS/ Rachel Murray)

Don’t Worry Darling was a troubled production to say the least. Two months after Harry Styles joined the production, Wilde split from her fiancé Jason Sudeikis and rumours swirled about Styles and Wilde’s relationship. At the same time, the media were reporting on a feud between Florence Pugh and Olivia Wilde

Styles and Wilde broke up in 2022, citing “different priorities.” In 2023, four months after his split from Wilde, Styles was seen making out with model Emily Ratajkowski in Tokyo.

Most recently, he got together with actress Taylor Russell, but that now seems to have gone the way of his previous relationships and flings.

Hopefully his trip to Rome to visit his bestie Alessandro will help him get over this latest breakup.

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