Stylist Tiffany Briseno has been working with Shawn Mendes for roughly six years, through music videos, press tours and album drops, but the 2022 Oscars represent a watershed moment in style for the singer-songwriter. “Except for a brief moment in the ‘Lost in Japan’ video, his fans and the rest of the world have never really seen Shawn in a look like this,” she tells The Hollywood Reporter.

At Sunday’s Oscars ceremony, Mendes is making his first-ever appearance on a red carpet in a classic tuxedo with bow-tie, a custom head-to-toe look designed by Dolce & Gabbana. The double-breasted black tuxedo is paired with a white tuxedo shirt finished with contrasting black buttons.

“We wanted a look that felt really classic and iconic and respectful of the event,” Briseno explains. “And because of Shawn’s [6-foot, 2-inch] height, he really looks great in double-breasted suits. We also thought a lot about the details, including a larger lapel with a single notch and patent-leather shoes. Overall it looks very luxe and classic; there’s definitely a 007 James Bond aesthetic.”

Shawn Mendes

Shawn Mendes attends the 94th Annual Academy Awards at Hollywood and Highland on March 27, 2022 in Hollywood, Calif.

Briseno only had about two weeks to put together a look, from the moment it was confirmed Mendes would join Sunday’s Oscars as a presenter. “As soon as we found out, we hit the ground running to make a custom collaboration happen,” she says. “This is Shawn’s first Oscars, so we knew it had to be something that felt special. It was super tight, but brands like Dolce & Gabbana are used to that. We knew they could pull it off.”

Several brands were enlisted to submit sketches for consideration based on Briseno’s early thoughts, then she and Mendes huddled together to edit the looks down to their favorites. “We both sat down with my phone in front of him, looking through everything and talking about different references,” she says. “He really fell in love with the idea of a double-breasted suit, so we ran with that. We’ve also worked with Dolce & Gabbana before; it’s a label that works well on him. As soon as Shawn put this suit on, we knew we didn’t need to try anything else. Those Italians really know how to cut a tuxedo.”

Indeed, Dolce & Gabbana sent a tailor from their Milan headquarters for Mendes’ fitting on Thursday in Malibu. “He spoke no English, and I don’t speak any Italian, so we had to have a translator,” Briseno remembers with a laugh. “But he was a genius tailor who definitely knew what he was doing. I watched him like a hawk for fitting tips.”

Mendes finished the look with several rings from his own collection, as well as a timepiece that had not yet been finalized by Saturday afternoon. “A tuxedo needs a watch to feel complete,” she adds.

Ultimately the tuxedo is the latest in Mendes’ style evolution, Briseno notes. “When we first started working together, Shawn sort of lived in classic leather jackets, T-shirts and skinny jeans,” she says, adding that her nickname for Mendes is “Dean,” as in James Dean, because of his penchant for pieces that feel classic and iconic. “Shawn has gone through everything from a rock ‘n’ roll stage to a 1940s dapper stage. But we’ve always focused on authenticity and incrementally growing into a style. And let’s face it, the man is a natural rock star, everything looks amazing on him.”

And make no mistake, tonight is special for Briseno as well. “Honestly, Shawn is like my brother, and I’m so proud of him,” she says. “The work we’ve done together has led to this moment, and I am really excited for him. Because we’ve never really done the tuxedo thing, to do it in this context feels pretty incredible. You never forget your first Oscars.”

This article originally appeared on The Hollywood Reporter.

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