1 of 37
DREW VS. KIM
The free-spirited wore her Catherine Malandrino gown with a belt for a Going the Distance premiere, while the reality shortened hers and added a bold necklace at the People’s Choice Awards.
2 of 37
GWYNETH VS. CAMERON
The upcoming Grammy wore her navy Burberry Prorsum coat with shearling boots in N.Y.C., while the bundled up in a scarf and brown riding boots in London.
3 of 37
JENNIFER VS. CHARLOTTE
The American Idol sported a striking Gucci jumpsuit with major bling at the launch of Gucci’s children’s line, while the Princess of Monaco went bare at a dinner for the brand.
4 of 37
NICKY VS. ELISABETH
The socialite wore her Alice + Olivia mini with equally glittery sandals in Monte Carlo, while the Mad Men star celebrated the show in black pumps and crimson lips.
5 of 37
HEATHER VS. JESSICA
Small-screen showdown! The Glee star goes preppy in her striped LOFT sweater, adding oxfords, while the Gossip Girl actress looks edgy in cut-out gloves and a hat.
6 of 37
RACHEL VS. KIM
The got sporty in her Smythe surplus coat in Toronto, while the dressed hers up in ripped jeans and lace-up boots while traveling.
7 of 37
JESSICA VS. VICTORIA
90210’s sexy star added edge to her Rebecca Minkoff lace-panel dress with intricate shoes at Comic-Con, while the teen sensation wore ladylike chain-strap pumps at a Hollywood party in October.
8 of 37
STACY VS. VANESSA
The blonde bombshell wore her Pleasure Doing Business mini with fuchsia pumps at a magazine event, while the rocked hers with black platforms in Las Vegas.
9 of 37
10 of 37
CHLOE VS. HAILEE
‘Tween trendsetters! The 13-year-old Kickass star wore her lacy Stella McCartney frock with tights and Mary-Janes in London, while the 14-year-old Oscar nominee wore an updo and added booties for an party.
11 of 37
KATE VS. KIM
The wore her tiered Nina Ricci with wavy locks to the 2010 Cannes Film Festival, while the opted for for more drama at this year’s Golden Globe after-parties.
12 of 37
JANUARY VS. KATE
The Mad Men actress rocked her chic Helmut Lang jacket for a day out in L.A., while the kept warm at Sundance by layering hers over a Dolce & Gabbana maxidress.
13 of 37
TAYLOR VS. COBIE
The Gossip Girl added rock&roll edge to her Alice and Olivia ruched mini on the show’s set, while the How I Met Your Mother star kept hers simple.
14 of 37
HALLE VS. NICKY
The layerd her David Learner sweatshirt over a T-shirt and black skinny jeans, while the socialite wore the same top in gray with ripped jeans and aviators.
15 of 37
CARRIE VS. GABRIELLE
The wore her Nicole Miller mini with a scarf to host the Country Music Awards in 2008, while the actress hosted dared to bare at this year’s BET Honors.
16 of 37
JESSICA VS. KHLOE
The Little Fockers glowed in a green Alexander McQueen gown in 2007, while Khloe paired the same strapless dress in gray with her short-lived red locks.
17 of 37
ASHANTI VS. KATY
The R & B diva picked a patterned one-shoulder gown from Kate Middleton fave Issa for an event in November, while the "Firework" opted for a down do and a coordinating cuff a month later.
18 of 37
JESSICA VS. MEGAN
took a layered approach to her low-key look, wearing her Rails button-up with a tee, leggings and boots, while the simply added a baseball cap and yoga pants.
19 of 37
KATHERINE VS. VANESSA
Though both had a similar approach to their Heartloom cardigans, kept hers conservative with an updo and turtleneck, while played up her boho style with long necklaces and loose locks.
20 of 37
EMMY VS. ASHLEY
The Shameless star mixed prints like a pro, pairing her Henry & Belle skinny jeans with a striped tee and a leopard scarf, while the Twilight traveled casually, wearing hers with boots and a slouchy sweatshirt.
21 of 37
ROSAMUND VS. ALEXA
Battle of the Brits! The actress wore her Christopher Kane astral-print dress with a gold clutch in New York City, while the TV host kept hers simple with sandals in London.
22 of 37
NICOLE VS. KELLY
The modeled her Lanvin goddess gown with gold accessories in Beijing, while the Gossip Girl star paired hers with sparkling jewelry and clutch in N.Y.C..
23 of 37
VANESSA VS. MARIA
The to be wore her Alice + Olivia dress with pointy-toed pumps, while the TV host spiced hers up with a multi-chain necklace at a Super Bowl event.
24 of 37
CATT VS. NICKY
The E! star wore her Minkpink dress with patent pumps to a Gilt Groupe party in L.A., while the socialite added a jacket and leggings to hers in Beverly Hills.
25 of 37
KOURTNEY VS. NICKY
The reality star blinged out her Ani Lee two-tone dress with a bib necklace and black pumps for a TV appearance, while the socialite kept hers simple with bangles and nude heels at a Gilt Groupe party in L.A.
26 of 37
EMMA VS. KIM
The stepped out in London in her studded Burberry Prorsum trench and lace-up boots, while the amped up the studs on her version of the same coat and added cap-toed Louboutins in N.Y.C.
27 of 37
GINNIFER VS. CHLOË
Big Love’s star paired her flirty Dior frock with turquoise earrings and patent sandals at an L.A. event, while the 14-year-old actress added tights and booties to hers in London.
28 of 37
CAMILLA VS. CASSIE
From Prada to Nada’s star rocked her Superdry cardigan with layered necklaces and demure hat in L.A., while the ABC Family star wore hers with a tee and furry topper in Park City, Utah.
29 of 37
ELLEN VS. EMMA
The Grey’s Anatomy paired her Gerard Darel parka with baggy jeans, while the young actress wore her black version with sleek skinnies.
30 of 37
JESSICA VS. JESSICA
dressed up her Madewell “Wide Legger” jeans with a sharp jacket and sunglasses, while the expectant stayed comfy in a plaid button-up.
31 of 37
NAYA VS. RUTINA
The Glee mean girl rocked her printed Christoforos Kotentos dress with bright red pumps at a Fox party, while the True Blood actress choose simple black accessories.
32 of 37
NATALIE VS. KIM
The Oscar accented her $199 Lanvin Hearts H&M dress with an updo and red lips, while the kept her look natural.
33 of 37
JESSICA VS. RACHEL
The accidental got all warm and fuzzy in her Christopher Raeburn parka, while the topped off a funky look with hers.
34 of 37
MARISA VS. DEBI
The Oscar winner wore her leaf-print Vivienne Westwood dress with drop earrings and stacked bangles, while the Entourage star played up hers with pointy-toed pumps.
35 of 37
EMMY VS. RACHEL
The Shameless actress wore her oatmeal Gerard Darel sweater with cozy footwear and hot-pink lips, while the paired her ivory version with her favorite boots.
36 of 37
CHERYL VS. KYLIE
The X Factor judge let her Emilio Pucci minidress shine on stage, while the Aussie singer punched up hers with metallic accessories.
37 of 37
REBECCA VS. DENISE
The wore her slinky Alice and Olivia shift with studded booties and a cuff, while the added only simple peep-toes.
Vote on More Fashion Faceoffs >
Kylie Jenner Shares Lip Kit and Ring Updates (Lucky You)
Vanessa Hudgens Just Brought Back Her Extensions (and They're Red)!
This Is the One Place Aly Raisman Is Dying to Take Taylor Swift Shopping
Kendall Jenner Talks About That Pre-Vogue Cover Shoot Haircut
Hailey Baldwin: My Dad Stephen Does Not Love My Booty Shorts