Gray was one of the first artists to use her body as a human billboard, but she didn’t look pretty doing it. The singer looked uncomfortable in this floor-length dress, which read as tacky on all accounts. “Wow, her outfit really makes me want to buy her new album,” said no one of the ensemble.
Miley’s Crop Top and More: 20 Questionable Outfits from VMA History
From the bold to the bad to the barely-there, we look back at some spectacularly memorable fashions from the MTV awards show
Macy Gray, 2001
Full List
Worst VMAs Looks of All-Time
- Miley Cyrus, 2013
- Rita Ora, 2012
- Nicki Minaj, 2011
- Deena Cortese, 2011
- Lady Gaga, 2010
- Perez Hilton, 2009
- Jennifer Lopez, 2009
- Britney Spears, 2007
- Brooke Hogan, 2004
- Paris Hilton, 2003
- Christina Aguilera, 2002
- Macy Gray, 2001
- Justin Timberlake, 2001
- Lil Kim, 2000
- Pamela Anderson, 1999
- Gwen Stefani, 1998
- Rose McGowan, 1998
- Kennedy, 1994
- Howard Stern, 1992
- Julie Brown, 1989