Wednesday night fashion industry leader Fern Mallis spoke with thee Marc Jacobs in front of a packed audience at the 92nd Street Y on Manhattan’s Upper West Side as part of the Fashion Icons interview series. We laughed, we cried and we were inspired by the story of the 49-year-old designer overcoming setbacks in his health, addiction issues and bad press—and somehow prevailing.

Despite being the youngest designer to receive the coveted CFDA award in 1987, the name behind several successful clothing and accessories lines and the Creative Director at Louis Vuitton for 15 years, Jacobs appears remarkably down to earth. He even admits he's still insecure and questions whether he has “made it.” 

That and he dropped hints about his upcoming Fall 2013 cosmetics line collaboration with Sephora.

Highlights from the talk below: 

On Joan Rivers, who Jacobs’ father, talent agent Steve Jacobs, represented via the Morris Agency back in the day:

“I read in some article that she said, ‘If I knew that brat of Steve Jacobs was gonna grow up to be Marc Jacobs I would have been a lot nicer.’”

On creating the lower-priced, but equally cool, Marc by Marc Jacobs clothing line:

“It was our idea. Both Robert and I love things that are as honest as a cotton T-shirt for 12 bucks, just as we love a cashmere sweater, as we love a duchesse satin dress… it’s an opportunity for design. The integrity of design. You go at them all with the same passion, and it’s great to reach more people. You can’t do that with fur and sequins.”

On his love of tattoos:

“I have 33. My good friend who is an artist, he’s done most of [them]—Scott Campbell. My Favorite? A Jean-Michel Frank couch. And ask me ‘Why a couch?’ because everybody does. And there’s no reason; that’s exactly the reason.”

On why his critically acclaimed September 1992 Grunge Collection (that didn’t sell well at all, by the way) was his most memorable and liberating:

“It’s like the stars were all in line. I was very inspired by this certain group of girls who really were the antithesis of what was considered perfect, beautiful and glamorous. There was something awkward. There was Kate Moss... and photographers like Juergen Teller and Corrine Day, David Sims. There was music happening like Nirvana, Pearl Jam, Sonic Youth. I just felt like there were all of these forces saying the same thing. There was this angst and there was this sort of feeling like, ‘Something’s gotta change.’ And it wasn’t punk and it wasn’t hippie. It was a different kind of movement. There was something very honest, very real saying, ‘I’m perfectly imperfect and I’m just as glamorous as I want to be. I wear a flannel shirt and no makeup… and look as just amazing as you do.” So, I guess there was that ’FUCK OFF’ thing.”

On Jacobs’ desire to not handle the business side of things; in particular, his appointment at Artistic Director for Louis Vuitton in 1997:

“You’ll have to ask Robert [Duffy, Jacobs’ business partner since 1984]…. I don’t know. Lawyers start talking and I go zzzzzzzzz. If you want to show me 50,000 swatches of duchesse satin, I’m an attentive audience. But when lawyers start talking? Or an accountant? I’m not really good at staying within a budget.”

On his ulcerative colitis and becoming healthy after Sonic Youth’s Kim Gordon referred him to nutritionist Lindsey Duncan:

“I stopped believing in medicine and started believing in nutrition, and taking care of yourself. Lindsey Duncan said, ‘I’m going to change your life.’

I had to take a nap every day, I had to laugh every day, I had to sweat every day—go to the gym, do yoga, get out of the office. And I drank green kale, wheat grass, egg whites, juices. No white flour, no dairy from a cow, no caffeine for the first year at all. I was 100% compliant. It was incredibly hard. I cried.

I go to David Barton [gym] 5 days a week. 2 hours a day. There are a lot of really nice looking people there. I’m still insecure about the way I look… I have issues. But I feel better. And I have my colon.”

On the contents of his bucket list:

“What’s that?”