09/19/2012 02:42 pm ET Updated Oct 11, 2012

Rachel Roy Style Evolution: From Wearing Pajamas In Public To Sitting Front Row With Kim Kardashian (PHOTOS)

We all have that one friend, who no matter what they wear (it could be an industrial-size garbage bag), they look amazing. And among New York Fashion Week's all-black wearing designers, Rachel Roy stands out in her mash-up of busy prints and ladylike demure -- surprisingly, it takes her less than an hour to get ready.

"I don't plan too much in advance. It all depends on how I feel that morning," explains Roy. "I dress on emotion and let that lead the way for what I wear and how I do my hair and makeup. I like the feeling of being a chameleon."

While the California-born beauty's style has certainly transformed since her days as the midriff-donning wife of Roc-A-Fella Records co-founder Damon Dash, one thing that has remain consistent is her knack for effortlessly mixing and matching -- a skill she admits her oldest daughter has helped her to perfect.

"Ava wears a lot of my RACHEL Rachel Roy collection -- she's a muse to me with how she mixes it," says Roy. "I really believe in taking risks to create things that feel authentic and individual. I think if you stop trying new things whether it be with fashion, food or the world, then you tend to get stagnant."

A belief we're sure she shares with her reality star BFF Kim Kardashian, who Roy describes as "truly a loyal friend." She adds, "If you confide in her, she will never tell a soul." Well, that explains the whispering between the two while sitting front row at Marchesa.

After wrapping up her spring 2013 presentation at fashion week, we're taking a look back at Roy's style over the years. Check out her evolution in the slideshow below, with captions written by the designer herself on some of her most unforgettable fashion moments.

Meanwhile, find out Rachel Roy's secret to looking forever young.

Flip through our many other Style Evolutions.

Want more? Be sure to check out Stylelist on Twitter, Facebook, Tumblr and Pinterest.

Rachel Roy Style Evolution