Cindy Crawford Covers Michigan Avenue November 2014

Her modeling career is the definition of successful longevity and Cindy Crawford is the cover girl for Michigan Avenue magazine’s November 2014 issue.

The former “House of Style” host celebrated the release at a snazzy soiree held at Chicago Cut Steakhouse on Tuesday (October 28), parading around in a form-fitting Alexander McQueen dress and a Cavalli necklace with Sergio Rossi heels.

In her cover story, Cindy talks about balancing her motherly duties with those of her business- “Well, the great thing about having kids is you don’t have to figure out your priorities anymore because you’re looking at them. It’s kind of great because it does prioritize your life in a whole new way. And you learn to say no more. I agree that you can have it all; I just think it’s really hard to have it all at the same time. So I just don’t do as many extracurricu­lar things, because I always have something better to do, which is being home with my family.”

Crawford also shared some advice she’d give her 18-year-old self- “You know, I think I would [tell myself] two things. One is, you’re good enough. I think young people—and adults—are plagued by our insecurities. [Mine was] coming to Chicago and coming to your studio and going to New York, and worrying that I didn’t belong or I didn’t deserve to belong, or whatever…”

“The other thing I would tell my young self is to just let loose a little bit more and have fun. I was very cautious and careful—which probably helped lead to the career that I had—but there were a few times I could have had a little bit more fun. Also, for me coming from such a sheltered small town, going to the big city and being around all that craziness of the ’80s, it was easier for me to put my nose in a book and just kind of block it all out.”

She added, “I didn’t quite know how to navigate it, so I just chose not to. But looking back, I was like, Maybe I should have gone on Armani’s boat for a week, or do things that [I didn’t do because] I was afraid of feeling out of my league or in an uncomfortable situation. Look, in the end it worked out for me, and I have a great life. Actually Rande has brought more [of that out in me]; he’s fun, and I feel safe having fun around him, so I’m almost doing some of those things. We used to go to the South of France every summer with his friends, and I would be like, That’s my one week a year that I dance on top of a table every day at lunch.”