For the past five years, Jack Sivan has been running a small tailoring and menswear business from the Brooklyn apartment he shares with his wife and their three guinea pigs — Bagel, Panda, and Faun. But with growing demand and recognition, he’s begun thinking about expanding his operations beyond the home studio.
This year, his brand gained unexpected prominence when actor Ato Essandoh, star of Netflix’s The Diplomat, wore one of Sivan’s custom tuxedos to the Screen Actors Guild Awards in February. The bold ensemble featured a cropped midnight blue jacket with satin lapels, a crisp white shirt, a black bow tie, and a dramatic long pleated skirt that nearly reached the floor.
“When I put it on, it just felt good,” said Essandoh, crediting his stylist John Tan for the introduction to Sivan. “Sometimes you wear something and it feels right. It felt regal and I loved the way that it flowed.” The outfit made waves among his peers — even drawing praise from fellow cast member Keri Russell and Abbott Elementary actress Sheryl Lee Ralph, who exclaimed, “Boy, look at what you’re wearing!”
Shortly before this red carpet moment, Sivan secured his first wholesale account with Ford General, a Chicago store that will begin selling his ready-to-wear collection in May. The line includes pieces like a double-breasted linen blazer ($1,155), striped linen pants ($575), and a military-style jacket ($685).
Custom suits from Sivan start at around $2,200, with prices depending on fabric and design details. His apartment near Prospect Park doubles as his workshop, filled with sewing machines, materials, mannequins, and clothing patterns. On a recent visit, mannequins wore designs like a pinstripe chore coat in Italian shetland flannel wool and a brown coat with pins still marking the collar.
Though most clients come seeking traditional suiting, Sivan’s skirted styles have also attracted growing interest. At a pop-up shop last September in downtown Manhattan, a skirt suit displayed in the window drew attention from people of all ages and genders.
“That brought in a lot of people,” said Persephone Bennett, a 29-year-old associate designer for Sivan. “They were like, ‘That is interesting to me and I want that.’”
Sivan acknowledges that other designers — including Thom Browne, Jean Paul Gaultier, and Yohji Yamamoto — explored skirted menswear long before him. However, his own take focuses on inclusive cuts inspired by 1970s flared tailoring and feminine silhouettes. “Each thing I’m making, maybe the decisions are small, but someone’s identity is in those decisions,” he said.
To emphasize that inclusivity, he features models like Lauren Ezersky, a 70-something former fashion TV journalist, and Nikhil Kapoor, a plus-size influencer, in his campaigns.
“A lot of the narrative around popular tailoring is that it’s very conformist,” Sivan said. He aims to change that perception with pieces that blend elegance and self-expression.
A graduate of the Rhode Island School of Design, where he studied apparel design and met Bennett, Sivan previously freelanced for The Row and denim brand R13. He grew up in Brookline, Massachusetts, and discovered a love for fashion in high school.
“The concept of clothing as language was novel to me,” he said. “It caught my interest at an age when most young people are coming to terms with who they are.”
In 2020, during the early days of the COVID-19 pandemic, Sivan began producing masks like many others in the garment industry. But with the lockdowns giving him more time, he also focused on growing his custom tailoring business. Many of his clients had never worked with a tailor before.
“Suddenly, a world of opportunities opens up,” he said. “And they’re just like, ‘Actually, I do care what kind of pocket shape I have on my jacket.’ Or, ‘I do really care that this waistband is a little bit higher.’”
Sivan has noticed a shift in attitudes toward formalwear. After years of increasingly casual dress codes, he’s excited by a renewed interest in suiting.
“It was concerning how the needs for suits were kind of disappearing,” he said. “Really, the only job that still requires a suit these days is if you’re a lawyer. But I think what that’s turned into is a realization that a suit doesn’t have to be a uniform. It can be a fun thing. It can be casual. It’s just a matching set.”
In essence, Jack Sivan’s designs breathe new life into suiting — combining craftsmanship, inclusivity, and a refreshing departure from convention.
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