CHRISTINA VS. NAOMI
The pop star covers up in her Juicy Couture tweed coat heading out in New York City, while the actress gets ruffled in her beige version at a Big Apple screening.
My Pick: Christina! You can imagine someone like Naomi to carry off a tweed coat but Christina rock this one out. She's looking better every day.
GWEN VS. PATRICIA
The singer rocked out in her plaid Vivienne Westwood gown at the 2004 Billboard Awards, while the newlywed actress – with husband Thomas Jane – celebrated at a Scottish fashion event in hers last month in L.A.
My Pick: Alright, this one is a shoo-in for Gwen. Patricia looks simply "off" and her boobs look like they're about to explode. And, the hair... ugh.
VICTORIA VS. MILLA
The British fashionista takes her mod Jovovich-Hawk mini out shopping in London, while the actress – and designer of the dress – hits a morning talk show in New York City wearing hers over jeans.
My Pick: Milla wins hands down! The fem-bot, Victoria can take the back seat. Then again, this look is can look nice both ways but Victoria Beckham is not cool in my book.
KATIE VS. RACHEL
It's the hot look for new moms! Holmes went shopping in Beverly Hills in her belted YSL tunic and jeans, while Weisz paired hers with a gray flannel skirt for a screening at the Toronto Film Festival.
My Pick: This is a toughie. But I like Rachel Weisz's look better than Katie's. Classier and more refine.
LINDSAY VS. SIENNA VS. NICKY
The Bobby star dazzled in her flowered Pucci minidress for a night out in London, while the British actress took the spotlight at the line's show. And Hilton took to the red carpet in the popular dress in L.A in September.
My Pick: Ooh, I heart this dress! My vote goes to Sienna - love those stockings!
ROSARIO VS. IVANKA
The actress went for silver in her metallic J. Mendel stunner at the Costume Institute Gala in New York, while Ivanka trump tied hers on for an event at the Natural History Museum in New York City.
My Pick:It's a hot dress and I think Rosario looks better as her skin tone reflects beautifully with this dress!
LINDSAY VS. CAT
Always the fashionista, Lohan pairs her Pucci dress with cropped leggings at a fashion event in N.Y.C., while the So You Think You Can Dance host shows off the same frock during New York Fashion Week.
My Pick:More Pucci dresses! I'm so into leggings now. So Lindsay Lohan wins this round.
EMMY VS. NATASHA
Rossum is all innocence in her Anna Sui frock and headband at a party in L.A., while Richardson paired it with matte black tights for a more sophisticated take in New York City.
My Pick:Emmy Rossum looks like a doll. And, the headband suits the whole cutesy look. However. I'm not wow-ed by Natasha's stocking choice for this dress. Makes her look like a chambermaid.
Text & Images: People