Isaac Mizrahi has never been a man to follow a single path. For decades he’s been known for his contributions to the fashion world but his interests are broad and varied and cover a lot of other territory.

‘Isaac Mizrahi: Does This Song Make Me Look Fat?’
When: 7:30 p.m. Sept. 29
Where: City Winery, 1200 W. Randolph
Tickets: $40-$65
Info: citywinery.com/chicago

For some time now, Mizrahi, has been traveling one of these other paths popping up in cabaret clubs around New York City where he sings standards backed by a stellar band.

“I’ve been working at this for quite some time,” Mizrahi says. “I had a one person show Off Broadway in 2000 and before that I had gigs for at least three years in preparation for that.”

The hard work also led to a sold out two-week run at New York’s Café Carlyle earlier this year. He is now bringing the Carlyle show, which he calls “Does This Song Make Me Look Fat?,” to City Winery Chicago. Mizrahi’s band is led by musical director Ben Waltzer (piano) and includes Stefan Schatz (percussion), Joe Strasser (drums), Benny Benack III (trumpet) and Raviv Markovitz (bass).

Anyone who knows Mizrahi isn’t surprised by his dogged turn to music. Mizrahi, always a bit of a showman, admits to being one of those kids who wanted to put on a show for anyone who would listen.

“I started doing female impersonations when I was eight years old,” Mizrahi recalls with a laugh. “Anytime I could draw a crowd which was as much as possible, I would do Judy Garland or Barbra Streisand.”

In the show, Mizrahi sings standards while also riffing on among other things personal weight issues, sleeplessness and Jewish stereotypes, fusing performance art, music and comedy.

“This is basically cabaret, which is theater with liquor,” Mizrahi says. “How can that be bad? It’s one of the most fun things in the world.”

Mizrahi’s song choices cover a broad spectrum ranging from Cole Porter’s “Bad For Me” to Blossom Dearie’s “Figure Eight,” a song she wrote for the children’s show “Schoolhouse Rock.”

“It’s just this odd little thing about the multiplication tables that I think is so beautiful,” Mizrahi says of Dearie’s song.

As for his jazzy singing style, he says: “I have a trained singing voice but I feel like I’m a raconteur. I put a song across in the tradition of cabaret singing which hopefully finds its way into your heart and also tells a story.”

Finding inspiration in New York’s cabaret world isn’t hard. Mizrahi says he admires the work of Elaine Stritch and Earth Kitt (“They were great role models”) but it was Liza Minnelli who was full of advice.

“We were close friends for awhile and she taught me a great deal and helped me conquer stage fright. She understood how difficult it is to get on stage. It’s wrought with terror, darling, terror. But I’ve learned once you’re on, you’re on and it all goes away.”

An impresario of high fashion in his early years, Mizrahi’s most recent designs have been found at Target, department stores (including Lord and Taylor), and online at QVC. He credits the 1995 documentary “Unzipped,” which followed Mizrahi as he planned his fall 1994 collection, with “opening a lot of other doors.”

“It made me realize more than anything that I might want to rethink the restructure of my life so that I wasn’t tied, ball-and-chain, to five fashion shows a year trying to recreate the wheel to entertain a bunch of editors,” Mizrahi says. “It really sort of unlocked me.”

As for those other interests Mizrahi is pursuing. He just finished taping another season as a judge on “Project Runway All-Stars” (airing in January on Lifetime) and is working on a memoir. He’s also forming a production company (“a very exciting prospect”) and is optioning Broadway, film and television projects.

“I knew that if I was going to fulfill my abilities and talents, I would have to broaden and that’s kind of what I’m in the middle of now. I’m so proud of everything I’m doing. I feel it’s really, really good to wake up every day and have all of this as the more important part of my day.”

Mary Houlihan is a local freelance writer.