Last month, Osbourne signed on as the latest face of Madge and daughter Lourdes Leon's Material Girl clothing line, which is in its second season. The reality star and "Fashion Police" co-host lost 50 pounds in 2010 and appeared on ABC's "Dancing with the Stars."
"It's such an honor to be a part of this campaign and it was an amazing experience to work with Madonna and Lola. Material Girl is incredible because it's high fashion but it is accessible to everyone at Macy's," Kelly Osbourne said in a statement. "I take so much of my style from Madonna in the 80s and I really admire how Lola dresses and that she stays true to herself."
Fashion photographer Brooke Nipar, former Photo Director of the now defunct Missbehave magazine, shot the photoshoot at various dive bars in New York City's East Village, including Lit Lounge and Mars Bar.
"I don't think I've ever been so nervous to meet someone in my entire life," Osbourne said of meeting Madonna. "But I think meeting Lola first and seeing how amazing and well-mannered and how lovely she is, you know your children are a reflection of your parents, so it made me a little less nervous. But at the same time, it's Madonna!"
In the behind-the-scene footage, Osbourne and Leon talk about their first meeting at a Jay-Z concert and how they were mutually star-struck.
"I met her before at a concert and I loved what she was wearing," Lola Leon said of Osbourne. "Just in general, she has amazing style and she's so sweet. She's awesome... [the line] is modeled after my mother obviously from that time, that Material Girl era."
Last year, Taylor Momsen of "Gossip Girl" modeled the Material Girl's first season.
The Material Girl line is available exclusively at Macy's and Macy's online.