Last Night's Look: Love It or Leave It?

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BRITNEY SPEARS

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Celebrating her lingerie line, The Intimate Britney Spears, in Oberhausen, Germany, the goes with a custom Michael Costello suit with a boudoir-inspired (of course) Maje cami underneath. (Not to mention that cute new haircut.)

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KATIE HOLMES

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The of Olay opts for a palette of all steely blues in a polished blazer and skinnies – and keeps her beauty look equally sleek with a chignon and defined lip at the premiere of Days and Nights in NYC.

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BROOKE SHIELDS

Dimitrios Kambouris/Getty

We’ve never thought of matching our statement necklace to our highlights before, but Brooke provides the inspiration with an outfit composed of various earthy browns and golds for the premiere of Days and Nights in NYC.

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LEIGHTON MEESTER

Future Image/Startraksphoto

The picks a playful Emilio Pucci mini that boasts both cutouts and color-blocking for the launch of St. Rillian fragrance in Tokyo.

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NICOLE SCHERZINGER

Mike Marsland/WireImage

The singer’s look for the #SingOne4TheBoys Karaoke Night in London is all about her standout accessories: the wide-brimmed hat, pop-of-color purse and cutout heels.

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HILARY DUFF

Ben Gabbe/Getty

The dresses up a cozy Stella McCartney sweater and skinnies with a selfie-worthy red lip and white IRO Klara booties for a stop by The Elvis Duran Z100 Morning Show in N.Y.C.

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BRITNEY SPEARS

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She may be launching her intimates line (in Warsaw, Poland), but it’s what wearing over her lingerie we want to talk about: a fall-ready mesh-paneled Tadashi Shoji dress in burgundy paired with killer lace-up Oscar Tiye heels.

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ELSA PATAKY

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The actress heats up the Dark Seduction event in Madrid with leather pants that show off her killer bod (just six months after having twins!), a printed lace-trimmed tank and ankle-strap stilettos.

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SARAH JESSICA PARKER

Gary Gershoff/WireImage

To kick off the New York City Ballet’s Fall Gala, the dance company’s vice chair () steps out in a heavily embroidered gown by Mary Katrantzou, who also outfitted dancers for the evening’s performance.

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NATALIE PORTMAN

Rabbani and Solimene Photography/Getty

For her appearance at the New York City Ballet event, opts for a baby-blue-and-white dress with a coordinating ivory clutch and nude slingbacks, much more muted than the bright Christian Dior number she wore to the gala last year.

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JESSICA CHASTAIN

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Anyone who’s ever said “redheads shouldn’t wear pink” should be required to study this photo of Jessica Chastain, looking sweet and chic in DSquared2 and perfectly-matched Christian Louboutins at the San Sebastian Film Festival in Spain.

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JULIANNE MOORE

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The actress, who is also a front-row fixture at basketball games, lets her shoes take center stage at the NBA 2K15 video game launch event in N.Y.C., matching her strappy, printed black-and-white pumps with a cream top and black ankle-length skirt.

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RITA ORA

Han Myung-Gu/WireImage

We have a lot to say about the British singer from seeing this unique getup, but we’ll leave it at this: She clearly loves to coordinate. For her the launch of her collaboration with Adidas Originals in Seoul, South Korea, she plays off her pumped up kicks, matching the neon hues with a paneled sweatshirt and pants (we’re talking about the ones under the shredded jeans), some wild highlights and more candy-colored accessories than we can count.

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CHLOË GRACE MORETZ

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At an AOL event in N.Y.C. promoting The Equalizer, Chloë showcases nautical chic, pairing her center-slit navy skirt with a striped top and two-tone pumps.

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CAMILA ALVES

JP Yim/Getty

At the Escada Meets Thilo Westermann collection launch in N.Y.C., Camila chooses a perky pink option from the brand’s Spring/Summer 2015 collection, pairing the breezy, bejeweled dress with her signature curls and metallic slingbacks.

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CHRISSY TEIGEN

Bryan Bedder/Getty

For the NBA 2K15 video game launch in N.Y.C., the model selects a bra top, toning down the sexy feel with a high-waisted skirt and sweater featuring sheer panels at the hem and sleeves.

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IVANKA TRUMP

Splash News Online

The businesswoman and mom shines in a metallic halter and matching sparkly sandals while enjoying date night at the New York City Ballet.

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JAMIE CHUNG

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Leave it to Jamie to sport a black tank and gray pants with major statement pieces, among them: a bib necklace, bold black-and-white checkered jacket and strappy pumps, to the NBA 2K15 video game launch in N.Y.C.

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KERRY WASHINGTON

Neilson Barnard/Getty

For the NYC launch of her Scandal collection for The Limited, picks a Giles Deacon frock with a flouncy peplum, bow-topped Roger Vivier heels and a cool fishtail braid with a few chic streaks.

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DIANE KRUGER

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Diane once told us that it “feels very natural” to call up her designer friends to ask for dresses. So we’re guessing that, to receive an award from the Paris Ministere of Culture, Diane was sent this high-necked Chanel Couture cocktail dress on a silver platter direct from pal Karl Lagerfeld.

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CHLOË GRACE MORETZ

Gilbert Carrasquillo/FilmMagic

One of our <a href="http://www.people.com/people/gallery/0,,20417681_20853638,00.html ">Best Dressed stars of 2014 defends her title at the NYC premiere of The Equalizer in a Dior Haute Couture dress with metallic embroidery that matches her silver sandals.

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CONNIE BRITTON

Paul Zimmerman/WireImage

Paging ! The Nashville star picks a Naeem Khan dress that could have come straight from the royal closet (a dainty-yet-bejeweled neckline and a modest hem) for the United Nations Equator Prize Gala in NYC.

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JEMIMA KIRKE

Taylor Hill/FilmMagic

What, like you don’t match your hair to you gown? The Girls star attends opening night of the Metropolitan Opera in NYC in her own inimitable style (and gives us the feeling we may see Lena Dunham trying this next).

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JESSICA CHASTAIN

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For The Disappearance of Eleanor Rigby premiere in San Sebastién, Spain, gives the candy-sweet Oscar de la Renta a dark spin with glossy dark wine lips.

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JENNIFER HUDSON

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We have to wonder which Jennifer has a larger collection of over-the-knee boots: or . At the Gilt City-hosted launch of her new album JHUD in NYC, the latter star shows off one of her many pairs in a graphic mini and silky tank.

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ASHLEY JUDD

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Light-hued bandage dresses are not for the faint of heart or unfirm of bod. Ashley, 46, proves she’s neither in a skintight, studded and scalloped version for a Sirius Radio appearance in NYC.

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BRIDGET MOYNAHAN

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For the season opening of the Metropolitan Opera in NYC, the actress chooses a Lela Rose gown with a starry crystal-encrusted top and the tiniest peplum on the skirt.

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TAYLOR SWIFT

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Newly crowned the Best Dressed star of the year, stuns in a bold but feminine Calvin Klein Collection ensemble and Christian Louboutin sandals at the iHeart Radio music festival in Las Vegas.

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JESSICA CHASTAIN

Karwai Tang/WireImage

The picks a yellow Erdem gown with a textured lace effect for a screening of Salome and Wilde Salome in London.

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UMA THURMAN

Paul Zimmerman/WireImage

For the Clinton Global Citizen Awards in N.Y.C., softens a serious buttoned-up vibe with feminine details like a lace skirt and dainty heels.

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SOPHIA BUSH

Steve Granitz/WireImage

For the iHeart Radio music festival in Las Vegas, Sophia opts for a body-con Monique Lhuillier with a circular large-scale mesh overlay effect and a geometric Rauwolf clutch that subtly mimics the motif of the dress.

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HILARY DUFF

Steve Granitz/WireImage

Also at the iHeart Radio festival in Las Vegas, the goes for a black-and-silver Anthony Vaccarello minidress with a statement ruffle that she accessorizes with gunmetal jewelry.

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ELLEN POMPEO

Imeh Akpanudosen/Getty

The Grey’s Anatomy star chooses head-to-toe chevron, wearing the pattern on a jumpsuit with a bold waist belt for ABC’s #TGIT event in West Hollywood.

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ELLE FANNING

Jason Merritt/Getty

Whoa, Ellie! The actress debuts a shorter dark brunette do that’s a far cry from the platinum blonde locks we’re used to. She goes dark with her outfit, too, choosing a black peplum top and trousers (both Oscar de la Renta) for the premiere of Boxtrolls in LA.

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KERRY WASHINGTON

Veronica Summers/Splash News Online

Gearing up for the new season of Scandal at ABC’s #TGIT event in West Hollywood, steps out looking way too quirky for Olivia Pope in a jacquard Mary Katranzou dress, SJP collection heels and a pearlescent Edie Parker clutch.

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EMMA WATSON

Robin Marchant/Getty

After speaking at the U.N. about gender inequality at the launch of HeForShe, attends the event’s afterparty in N.Y.C. in a look that’s all business: a Hugo Boss sheath and Roger Vivier heels.

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GINNIFER GOODWIN

Jon Kopaloff/FilmMagic

For the Once Upon a Time premiere in Hollywood, new mom Ginnifer goes totally ladylike in a top and skirt by Marni and über-girlie Christian Louboutin heels with an elegant silver accent over the toes.

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CAMILLA BELLE

Paul Archuleta/FilmMagic

At a fundraiser for Alex’s Lemonade in L.A., Camilla’s fresh blonde highlights and her white Shoshanna dress and pink sandals (with an adorable yellow accent on the heel!) are giving us warm weather nostalgia.

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IGGY AZALEA

Debby Wong/Corbis

The singer hits the red carpet (and the stage) at the iHeartRadio music festival in Las Vegas wearing a wild patchwork dress that, when she turns to the side, looks more like a supershort tunic over a leotard.

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Last Night's Look: Love It or Leave It?

1 of 39

BRITNEY SPEARS

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KATIE HOLMES

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BROOKE SHIELDS

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LEIGHTON MEESTER

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NICOLE SCHERZINGER

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HILARY DUFF

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BRITNEY SPEARS

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ELSA PATAKY

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SARAH JESSICA PARKER

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NATALIE PORTMAN

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JESSICA CHASTAIN

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JULIANNE MOORE

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RITA ORA

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CHLOË GRACE MORETZ

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CAMILA ALVES

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CHRISSY TEIGEN

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IVANKA TRUMP

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JAMIE CHUNG

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KERRY WASHINGTON

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DIANE KRUGER

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CHLOË GRACE MORETZ

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CONNIE BRITTON

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JEMIMA KIRKE

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JESSICA CHASTAIN

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JENNIFER HUDSON

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ASHLEY JUDD