News Awards & Events Grammys The Risk-Taker Awards By InStyle Editors InStyle Editors Facebook Instagram Twitter Our editors and writers comprise decades of expertise across the beauty, fashion, lifestyle and wellness spaces in print and digital. We prioritize journalistic integrity, factual accuracy, and also having fun with every story we share. InStyle's editorial guidelines Updated on January 26, 2010 @ 02:26PM Pin Share Tweet Email Trending Videos Photo: Gilbert Flores/Celebrity Photo The Risk-Taker Awards 01 of 07 Most Notorious Grammy (or Any Red Carpet) Dress Ever Award Eric Charbonneau/Berliner Studio Jennifer Lopez in Versace, 2000 02 of 07 All Bases Covered Award (Long? Short? Both!) Vince Bucci/Getty Images Eve in Jean Paul Gaultier, 2002 03 of 07 Best Diane Keaton as Ozzy Osbourne Impersonation Award Steve Granitz/Wireimage.com Sheryl Crow in Anton pants, 2000 04 of 07 Best Liner Notes KMazur/WireImage, Jeff Kravitz/FilmMagic Avril Lavigne in her own design and Converse sneakers, 2003 05 of 07 Razor-Sharp Tailoring Award Fitzroy Barrett/Globe Photos Missy Elliott in Versace, 2000 06 of 07 Most Riveting Artist Jeff Vespa/IPOL/Globe Photos Monica in D&G, 2000 07 of 07 Alternative Sheikh Award Gilbert Flores/Celebrity Photo Alicia Keys in Christian Dior, 2002