Jessica Simpson

2007

JESSICA SIMPSON

2003: Then a Newlywed, Simpson tried for grown-up glamour with an Armani pantsuit.
2004: She got white right in a sparkling Valentino dress paired with silver Christian Louboutin pumps.
2005: She was in saucy milkmaid mode in 2005 – thanks to her ruffled Rachel Roy top.
2006: Simpson went '80s retro in a sleek bob and second-skin vintage Azzedine Alaia micro-mini.