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Troye Sivan’s path to fame has been decidedly modern. Although he started out as a child actor (he famously played the younger version of Wolverine in 2009’s X-Men Origins: Wolverine), he didn’t really come into prominence until he launched a YouTube channel during the platform’s golden age of vlogging. Not content with a career limited to just doing things like the cinnamon challenge, Sivan began expanding to music in 2015 and has slowly won over a legion of new fans for whom the word “Troyler” (a nickname born from Sivan’s friendship with fellow YouTuber Tyler Oakley) means nothing.

Likewise, Sivan’s style has undergone a similar evolution. In his early red carpet days, the Aussie kept to a uniform of slim suits and button-ups like he was either a circa-2003 Hedi Slimane muse or an NME-approved indie rocker. Though, in recent years Sivan has grown into one of fashion’s most adventurous male risk-takers. Inspired by queer history and his own growing confidence, the 28-year-old is often amongst the first to bring some of men’s fashion week’s edgiest outfits to the red carpet.

2023: Loewe Show

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We had predicted the imminent arrival of “No Pants Trend” for men a few weeks before, and Sivan really delivered on that promise while sitting front row at creative director Jonathon Anderson’s Loewe menswear show. He paired an oversized pale yellow shirt with a pair of glittering brown Chelsea boots (and did in fact have a pair of tiny shorts on underneath).

2023: amfAR Gala

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Sivan’s Ferragamo number for the amfAR gala in France was a visual representation of the power of versatility: it was almost evening gown-inspired up top, with a more traditional black pant on the bottom.

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2023: Cannes Film Festival

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This custom Valentino look really deconstructed the idea of a traditional suit and tie look.

2023: The Idol Premiere After-party

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This Alexander McQueen cut-out tank is equal parts “tank” and “cut-out,” but Sivan pulled it off well for an after-party in Cannes.

2023: Vanity Fair Oscars Party

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If the “Rush” video is any indication, Sivan takes his “afters” seriously and he showed up to Hollywood’s biggest “afters” of the year, Vanity Fair’s Oscar party, in a full leather look from Diesel.

2021: Met Gala

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Working with stylist Mel Ottenberg for the night, Sivan’s 2021 Met Gala look proved to be a breakthrough moment for the singer’s personal style. He paired a halter dress from Joseph Altuzarra’s gender-fluid Altu line with a pair of Rick Owens’s signature Kiss boots, Cartier jewels, and a leather cuff around his arm. The full look also included Luar’s Ana bag and a jockstrap underneath it all.

2021: MTV Video Music Awards

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Sivan became an honorary leader in the nascent “male crop top” movement when he opted for this ab-baring Fendi set at the 2021 VMAs.

2020: Elton John Oscars Party

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Marking his last major red carpet appearance before lockdown, this all-blue Sies Marjan fit echoes his previous all-red Met Gala look.

2018: Variety Pre-Emmy Party

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When not in a full suit, a pair of skinny jeans and oversized button-up was also once one of Sivan’s go-to event outfits.

2018: Aria Awards

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Mind you, Sivan does look good in a relatively simple black skinny suit.

2018: Met Gala

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While still sticking to his skinny suit comfort zone, Sivan’s Valentino suit for the 2018 Catholic Imagination-themed Met Gala proved a taste of things to come with its unapologetically bright color and mesh shirt layered underneath.

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2016: MTV Music Video Awards

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A simple, well-executed outfit that also leaves little doubt that Sivan was once a circa-2014 Tumblr user.

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