An Inside Look at How Mahershala Ali Masters Red-Carpet Style

I’m chatting with Mahershala Ali’s stylist, Van Van Alonso, and she’s explaining what it is, exactly, that makes the Oscar-winner’s style so extraordinary. “Adding those personal touches, and making it a little more unique with the accessories and the textures,” she explains, are crucial elements when it comes to making a red-carpet look stand out. But there’s something more to it.

“Honestly, who wears it,” she says. “Mahershala, everything he wears, he’s just so magical. Anything he puts on, it’s like, ‘Wow, that guy looks great!’ It’s hard to go wrong with him. He can get away with a lot of things that other people can’t.”

At the 2017 SAG Awards.

Alonso should know. She’s been working with Ali since right around the time Moonlight made its way into the world in 2016, before the movie or Ali were household names and Oscar nominees—let alone winners. “It was really challenging,” she says. “Because compared to the interest now and how easy it is for us to get access to things, at the beginning it was completely the opposite.”

Still, awards season loomed. And Moonlight’s runaway critical success meant that the red carpet was mandatory. Luckily, Ali and Alonso had one brand ready to work with them from the start. “Some characters like Mahershala Ali are so bright and special, and they have such a unique and personal style, that there is no doubt I am attracted by them,” says Alessandro Sartori, artistic director of Zegna. “And that’s the first reason why we got in touch with his team.”

Ali wound up wearing the Italian label at both the 2017 SAG Awards (a white, shawl-collar tux) and Oscars (black tux, peak lapel). Both times, he walked away with a win. “I like doing memorable things with him, because he’s so special that I feel like that has to translate,” Alonso says. “We’re always on that custom situation. And that’s the thing with Zegna. When it comes to menswear, it’s hard to find what they offer.”

At the 2019 SAG Awards

She explains that the brand gives her and Ali access to the kind of fabrics and silhouettes that let them make the right impression. “We’re all about getting him the most unique things that nobody else is going to be seen in.”

That same mentality was at the forefront of Ali’s latest awards-season effort, this time for his role in Green Book. “When we discuss the looks, we go deep into every single detail,” says Sartori. Ali wore Ermenegildo Zegna XXX, the label’s couture collection, for both the SAGs and the Oscars. And in a case of history repeating itself, he once again walked away with wins.

At the 2017 Oscars.

Ali’s look for the 91^st annual Academy Awards was one for the record books, featuring a one-and-a-half-breasted jacquard dinner jacket, matching vest, and a stand-collar shirt with a vintage stone button. He paired it with custom aviator glasses from Cutler & Gross. But one piece in particular caught everyone’s attention. “The hat he wore at the Oscars was a very beautiful accessory that he decided to wear by himself to further personalize the outfit we made together,” Sartori says. The piece was, indeed, not from Zegna. Instead, the last-minute addition came courtesy of New York City-based milliner Gigi Burris.

“They contacted us on Tuesday, we shipped it on Wednesday, and they received it on Friday,” Burris says. Alonso and Ali had been discussing a hat—trading photos of everything from Jinnah caps to fezes—as part of the look. But didn’t land on a favorite until they discovered Burris’s “Sharina” model, which is made of rabbit-fiber velour and blends a structured crown with the laid-back vibe of a casual knit cap. It’s “basically a cooler, more put-together version of a beanie,” Burris says. But despite the seemingly perfect fit, Burris had her reservations.

“We get a lot of requests for situations like this, and nine times out of ten, they don’t end up wearing the piece on the carpet or performing or whatever. Because hats are such a punctuating part of the outfit. They’re probably one of the most prominent accessories a man or woman could wear. So when this happened, I was so excited.”

But it wasn’t just about the hat making a big-time appearance. It was about who was wearing it. “He’s truly someone that I admire so much,” Burris says. “So it’s not only cool that it happened on the carpet—it’s cool that it happened on him.”

If there’s one thing that holds true through Ali’s many appearances—on the red carpet, or in the UK edition of Esquire—it’s that whether he’s wearing a tux or a neon-green suit, he always exudes the same kind of confident cool. When I asked Alonso about the hat, she offered up a question in reply. And sure, she’s talking about headwear. But you could also say she’s distilling down some more elemental about Mahershala Ali’s style: “Who else could do that but him?”