Celeb Fashion Hit or Miss?

Vote on this week's styles including Paris Hilton, Penélope Cruz and 28 more stars! You decide – are they fashionistas or flops? By Melissa Liebling-Goldberg

01 of 29

PARIS HILTON

PARIS HILTON
James Devaney/WireImage

The heiress makes a sophisticated entrance into The Late Show with David Letterman in a paneled bustier and pencil skirt.

02 of 29

PENéLOPE CRUZ

PENéLOPE CRUZ
Carlos Alvarez/Getty

The Spanish star celebrates the shooting of her new film with Pedro Almédovar in a chic belted little black dress in Madrid.

03 of 29

LAUREN CONRAD

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Scott Gries/Getty

The Hills star hits MTV’s Upfront Presentation in a peacock-print Elizabeth & James dress and long curls.

04 of 29

DIANE KRUGER

DIANE KRUGER
Dimitrios Kambouris/WireImage

The actress brightens up a Ferragamo party in N.Y.C. in a blue striped dress by the Italian label.

05 of 29

AMANDA PEET

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INF

Peet goes for the layered look at the opening of the Rogan for Target boutique at Barneys New York.

06 of 29

NICOLE RICHIE

NICOLE RICHIE
DS-ISM/SS/Flynet

The new mom turns up in a mixed-print Elizabeth and James dress, black Tom Ford fedora and vintage Gucci boots for classes at traffic school in L.A.

07 of 29

TAYLOR SWIFT

TAYLOR SWIFT
Ray Tamarra/Getty

The country singer is all uptown-chic in her glittering metallic Badgley Mischka shift at the 5th Annual Event to Prevent Benefit in New York.

08 of 29

GINNIFER GOODWIN

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Valerie Macon/Getty

The actress is honored as MaxMara’s “Face of the Future” in a abstract-print dress in Los Angeles.

09 of 29

MISCHA BARTON

MISCHA BARTON
Ray Tamarra/Getty

Another day, another pair of puzzling pants! The fashionista turns up in baggy high-waisted pants and a floral bustier to the 5th Annual Event to Prevent Benefit in New York.

10 of 29

EMMY ROSSUM

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Gary Gershoff/WireImage

The actress takes a classical stance in her pleated one-shoulder Carmen Marc Valvo gown and Cole Haan clutch at the 2008 Pratt Institute Fashion Icon Award show in N.Y.C.

11 of 29

BEYONCé

BEYONCEé
Jamie McCarthy/WireImage

How to avoid wearing a wedding band? Cover up with short gloves instead! The newlywed adds major Chanel bling to her little dress and gloves at a bash thrown by Jay-Z in N.Y.C.

12 of 29

NICOLE RICHIE

NICOLE RICHIE
John Shearer/WireImage

The new mom enjoys night out at a party for Stella McCartney in a simple white dress and cropped black jacket by the designer.

13 of 29

KATE MOSS

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Dimitrios Kambouris/WireImage

The model wears a feathered black vest and skinny jeans to celebrate her new Agent Provocateur ads at an N.Y.C. bash.

14 of 29

CHARLIZE THERON

CHARLIZE THERON
John Shearer/WireImage

Theron stays bundled up in her black coat at the Stella McCartney party in Los Angeles.

15 of 29

DIANE KRUGER

DIANE KRUGER
Andrew H. Walker/Getty

Following a night out at the Met Costume Institute Gala, the actress blooms in a floral Balenciaga dress at a spring lunch honoring Antony Todd. The event – held in N.Y.C.’s Grand Central Station – was hosted by “A Diamond Is Forever.”

16 of 29

HILARY DUFF

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Demis Maryannakis/Splash News

The actress turns up at a Allure photo exhibition of nudes with her black satin strapless Celine dress firmly on.

17 of 29

ANGIE HARMON

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Michael Buckner/Getty

Harmon gets bold in a Stella McCartney floral jumpsuit at the designer’s L.A. party.

18 of 29

KATE BOSWORTH

KATE BOSWORTH
Peter Kramer/AP

Talk about style superpowers! As a guest of Chanel, the lucky actress hand-picked her sequined vintage Chanel Haute Couture dress from the ’80s archives to match the superhero theme of the Met Costume Institute’s annual gala in N.Y.C.

19 of 29

CAMERON DIAZ

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Ray Tamarra/Getty

Skipping the Costume Institute bash, the actress leaves TRL in bold red heels and black J Brand skinny pants with her What Happens In Vegas costar.

20 of 29

MISCHA BARTON

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Evan Agostini/AP

Barton attends the Met gala in a custom-made Missoni gown with ruffled straps and a beaded bodice and Bulgari jewels.

21 of 29

PARIS HILTON

PARIS HILTON
Jason Merritt/FilmMagic

On the West Coast, the heiress mixes her florals with a printed dress and clutch for the Hornitos Tequila Cinco de Mayo party in Hollywood.

22 of 29

JOY BRYANT

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Gregorio Binuya/ABACA

Showing off a banged bob, the actress keeps covered in her geometric print Pucci gown for the annual Met gala.

23 of 29

ASHLEE SIMPSON

ASHLEE SIMPSON
Pastierovic/face to face/iPhoto

Still no sign of a baby bump! The petite singer adds a rock ‘n’ roll edge to a chic high-waisted pencil skirt with white pumps, a scarf and long beads for the Bravo Supershow in Germany.

24 of 29

CHRISTINA RICCI

CHRISTINA RICCI
Stephen Lovekin/Getty

Taking a break from the Speed Racer red carpet, the actress attends the Costume Institute bash in a sweeping Givenchy gown and Bulgari jewels.

25 of 29

HEIDI MONTAG

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Jason Kempin/WireImage

Giddy-up! The reality star adds on a bold pink hat to her strapless Ralph Lauren floral dress at the Kentucky Derby.

26 of 29

PARIS HILTON

PARIS HILTON
Jon Kopaloff/FilmMagic

The heiress is a riot of color and print on the Race to Erase MS red carpet in L.A.

27 of 29

CHRISTINA RICCI

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Demis Maryannakis / Splash News

The Speed Racer star plays peek-a-boo in her keyhole black Balmain dress, Manolo Blahnik heels, Romanek clutch, Chopard jewels and loose curls at the Tribeca Film Festival.

28 of 29

MOLLY SIMS

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Jason Kempin/WireImage

Sims gets into the spirit at the Kentucky Derby in her oversize black Eric Javits hat and feminine Ports 1961 gray dress.

29 of 29

MISCHA BARTON

MISCHA BARTON
Demis Maryannakis/Splash News

The actress makes a low-key style statement in skinny jeans and an ombré top at the opening night of Boeing-Boeing on Broadway.

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