He burst onto the fashion scene with his trailblazing designs in the 1980s, and now, Isaac Mizrahi is a household name thanks to successful collections for Target and QVC and a stint as a judge on “Project Runway: All Stars.” Now, he’s trying his creative hand at performing.

After selling out shows in New York City, Mizrahi’s “Does This Song Make Me Look Fat?” makes its Chicago debut at City Winery (1200 W. Randolph) Sept. 29. Here, he gives us the scoop on what to expect from his performance.

What’s the inspiration behind the show? I dropped a few pounds in the last two years, — literally a few. No one’s going to tell you the truth about [your weight]; others are always like, “Oh, you look fine.” Well, who is going to tell you? And are you going to believe them? It’s [the] edge I’ve lived on my entire life, whether it’s when I was 40 pounds thinner, or when I look at myself [now] and think, “Is it fat? Is it obese? Is it pleasantly plump? Is it old?” That’s what the show is inspired by, by not knowing who you are and yet knowing who you are.

The New York Times refers to your performance as a “fusion of standup and cabaret.” Why did you create the show in this format? Cabaret is this idea of responding to people’s amusement and building on it. If you put a Broadway show together, you’re going to do the same thing every single night with a few variations. But with cabaret, it really happens in a different way every single time. I could literally do it every night for the rest of my life and be very happy and never bored.

What was the writing process like in putting this show together? I e-mail myself [ideas] in order to not forget. Then, at some point [when] I have 15 minutes to write the thing, I have this sort of critical mass of stuff that I start putting into order. I start thinking about songs that would be really hilarious, or poignant, or beautiful … and that’s how the show gets written. [It’s] a very intense writing period.

Let’s talk fashion. How would you describe your personal style? Really practical — I feel like practicality is a big part of style. I don’t like to see people go out of their way too much to be stylish. A stripe is great, a print is great, but if it looks like someone tried too hard or can’t function in their shoes I immediately think it’s not working. It needs to be fun and funny — if there’s humor involved, you’ve got me.

What’s the biggest lesson you’ve learned in the fashion industry? The biggest lesson is to really work. If you believe in something and you keep doing it, you get better at it — you get so good at it that you stop failing.

For tickets to the show ($40-$65), visit Citywinery.com/chicago.