How Jack Sivan’s Nonconformist Men’s Wear Business Came to Be

Not long before dressing Mr. Essandoh, Mr. Sivan landed his first wholesale account with Ford General, a store in Chicago. In May, it will start selling pieces from Mr. Sivan’s burgeoning ready-to-wear line, which includes items like a double-breasted linen blazer ($1,155), striped linen pants ($575) and a matching military-inspired jacket ($685).

Mr. Sivan’s custom suits start at about $2,200; their prices vary based on fabrics and other factors. His business has taken over much of the living room in his apartment near Prospect Park, which has workstations with sewing machines and metal shelves where materials and clothing patterns are stored. There are also multiple mannequins that Mr. Sivan, 28, dresses in clothes he is making, which on a recent visit to the space included a pinstripe chore coat made of Italian shetland flannel wool and a brown coat that still had sewing pins in a pocket and the collar.

Most of Mr. Sivan’s customers have sought traditional suiting, but Mr. Essandoh has not been the only one to take interest in his skirted styles. Last September, at a pop-up shop Mr. Sivan opened in downtown Manhattan, a skirt suit was displayed in a window. “That brought in a lot of people, just all ages, all genders,” said Persephone Bennett, 29, an associate designer for Mr. Sivan. “They were like, ‘That is interesting to me and I want that.’”

Mr. Sivan, of course, started making skirted men’s wear long after other designers — Thom Browne, Jean Paul Gaultier and Yohji Yamamoto among them — introduced their own versions. His pieces are designed with a range of wearers in mind, he said, and tend to have curvier cuts that take inspiration from flared 1970s suiting and from women’s wear silhouettes.

“Each thing I’m making, maybe the decisions are small, but someone’s identity is in those decisions,” Mr. Sivan said. To help telegraph the inclusive nature of his clothes, people like Lauren Ezersky, a 70-something former fashion television journalist, and Nikhil Kapoor, a plus-size influencer, have been tapped to model them.