Obsessed or Hot Mess? Vote on These Daring Looks

THE FLOATING COLLAR

If you work at a conservative office or are invited to a buttoned-up event, but you don't want to deny the world a look at your décolletage, get a top like Alyssa Milano's, which offers the best of both worlds.

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Obsessed or Hot Mess? Vote on These Daring Looks

TIGHTS IN MAY

The sun is out, the temps are up, so the only possible explanation for why Zooey Deschanel is still in her black stockings is that she's been wearing them for so long, they're now permanently fused to her legs.

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Obsessed or Hot Mess? Vote on These Daring Looks

BANDEAUS & HIGH-WAISTED SKIRTS AS GOWNS

If your maxi skirt is too long, skip the tailor and simply hike it up to just below your strapless bra. Et voilà, a red carpet ensemble as classy as Shahs of Sunset star Golnesa "GG" Gharachedaghi's!

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Obsessed or Hot Mess? Vote on These Daring Looks

THE INVERTED SCOOPNECK

Because a girl can only wear so many plunging looks, Carey Mulligan tries a totally fresh neckline with the half-moon top of her Balenciaga by Alexander Wang jumpsuit.

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Obsessed or Hot Mess? Vote on These Daring Looks

HEADBANDS AT THE HAIRLINE

Normally, we can determine the type of event solely by the placement of an attendee's headband (forehead means outdoor music festival and holding back hair means red carpet), but British actress Carly Steel attempts to throw us for a loop with this split-the-difference style.

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Obsessed or Hot Mess? Vote on These Daring Looks

NECK BRACE TOPS

If you wear something like Gwyneth Paltrow's Céline turtleneck tank, don't be surprised if friends' reactions aren't, "I love your top!" but rather, "Are you OK?!"

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Obsessed or Hot Mess? Vote on These Daring Looks

BUTTON-DOWNS, UNBUTTONED

How embarrassing is it when you get to work and realize you didn't line the buttons up with the correct button holes and you're walking around with an asymmetrical shirt? Rihanna (in a Balmain blouse) has found the way to guarantee you never suffer that mortification again.

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Obsessed or Hot Mess? Vote on These Daring Looks

IRIDESCENT HEELS

It used to be that wearing metallic heels made you stand out. But with everyone running around in gold and silver pumps, Hilary Duff must have felt the need to step up her kick game and wear this pair of dazzling, light-reflecting shoes.

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Obsessed or Hot Mess? Vote on These Daring Looks

TUTU SKIRTS

Ballet flats have been a staple in our closets for years and leotards are now commonplace in Hollywood, so it's about time the one missing piece of a dancer's uniform – tulle skirts, like the navy one Zooey Deschanel wears – follows suit.

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Obsessed or Hot Mess? Vote on These Daring Looks

SUPER-LONG EARRINGS

When Willow Smith's "Whip My Hair" comes on, Maggie Gyllenhaal doesn't have leave the dance floor. Because what her hair lacks in length, her shoulder-grazing danglers more than make up for.

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Obsessed or Hot Mess? Vote on These Daring Looks

THE STAR NECKLINE

No V-necks, sweethearts or portrait collars for Michelle Trachtenberg (in Rachel Zoe Collection) and Ariel Winter (in Three Floor), who reinforce their star status by wearing celestial-looking cutouts at their décolletages.

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Obsessed or Hot Mess? Vote on These Daring Looks

STAR-PRINTED BOTTOMS

Speaking of stars in stars, Alessandra Ambrósio and Kate Hudson make some stellar additions to their wardrobes via Big Star cutoffs and 291 sweats, respectively.

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Obsessed or Hot Mess? Vote on These Daring Looks

FANCY OVERALLS

Normally overalls make us think of the line from Clueless, "She could be a farmer in those clothes." But Ashley Madekwe is out to prove onesies can be chic with her checked jumpsuit by Topshop.

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Obsessed or Hot Mess? Vote on These Daring Looks

BOW TIES ON DRESSES

We're really hoping Justin Timberlake will follow up the anthem of bow-tie-wearing men everywhere ("Suit & Tie") with the lady version, "Gown & Tie." And when he does, Kate Mara will be ready.

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Obsessed or Hot Mess? Vote on These Daring Looks

OVER-THE-COLLAR NECKLACES

Men complain about having to wear neckties every weekday, but do you have any complaints about Olivia Palermo wearing the jewelry equivalent of one over her collared Rochas jacket?

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Obsessed or Hot Mess? Vote on These Daring Looks

HIPPY DRESSES

After decades of searching for dresses that make their hips look smaller, women (namely Michelle Williams in Kate Ermilio, along with Sophia Bush and Dianna Agron) opt to add inches to their silhouettes via these voluminous designs.

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Obsessed or Hot Mess? Vote on These Daring Looks

SLEEVE CUTOUTS

You've seen them on abs, on thighs, on décolletages, but Victoria Beckham sports slashes in a totally new location: her forearms.

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Obsessed or Hot Mess? Vote on These Daring Looks

THE BROADWAY CURTAIN DRESS

Doesn't Alessandra Ambrósio's mini remind you of the opening act of a play? And in this show, it appears the spotlight-stealing star behind the curtain is her hot body.

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Obsessed or Hot Mess? Vote on These Daring Looks

ALLOVER STUDDED PANTS

Whatever your opinion of Kourtney Kardashian's spiky black skinnies, we can all agree they're preferable to Justin Bieber's spiked hat, right?

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Obsessed or Hot Mess? Vote on These Daring Looks

WIDE-LEG, CROPPED JUMPSUITS

With everyone and their mother wearing these onesies, Gwyneth Paltrow clearly has to take the trend to the next level and make it all her own by wearing a Barbara Casasola design with a plunging sheer panel and bell-bottom legs that hit at the calf.

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Obsessed or Hot Mess? Vote on These Daring Looks

THE INVERTED V HEMLINE

The "cavewoman" hemline, which is shaped like an M, didn't win you over, but perhaps this one (seen on Molly Sims), shaped like another letter of the alphabet, will.

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Obsessed or Hot Mess? Vote on These Daring Looks

PATCHWORK DENIM

For those days when wearing a chambray shirt with jeans just isn't enough to satisfy your denim cravings: Reach for a dress like Chloë Moretz's Louis Vuitton one that combines many swatches, all stitched together.

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Obsessed or Hot Mess? Vote on These Daring Looks

SEE-THROUGH SHOES

We're hoping Winona Ryder's translucent plastic heels don't catch on for the sole reason that if they do, we'll have to start getting pedicures before sandal season.

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Obsessed or Hot Mess? Vote on These Daring Looks

HIGH-NECK SHEER BLOUSES

This is a momentous occasion! Never before have the words sexy and turtleneck been uttered in the same sentence. But Miranda Kerr knows there's a first time for everything.

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Obsessed or Hot Mess? Vote on These Daring Looks

KNEE-HIGH GLADIATOR SANDALS

Russell Crowe's character gets the thumbs up from the emperor while wearing these in Gladiator, but do Kourtney Kardashian's Chanel and Selena Gomez's Versace versions get your approval?

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Obsessed or Hot Mess? Vote on These Daring Looks

MATCHING BUTTON-DOWNS & BLAZERS

Emmy Rossums's Carven topper is printed with a map of Paris, but just in case she heads to the City of Light then accidentally leaves the blazer behind in a café, she also has a shirt with the exact same geographic imagery.

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Obsessed or Hot Mess? Vote on These Daring Looks

OVERALLS ... WITH CROP TOPS

Her smock-front denim onesie may be farmer-inspired, but as soon as Diane Kruger turned around to reveal she's wearing a shrunken tee, we realized this outfit is all about fashion, not fieldwork.

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Obsessed or Hot Mess? Vote on These Daring Looks

EXTREME HIGH-LOWS

No, we're not talking about an up-and-down, roller coaster relationship, but rather Kourtney Kardashian's silk salmon top, which hits at her hips in the front and grazes the ground in the back.

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Obsessed or Hot Mess? Vote on These Daring Looks

SOCKS WITH SNEAKS

We can all agree that this combination is acceptable when playing in a tennis match and commuting in the big city in the year 1984, but Emma Roberts is doing neither so we're going to put this one to a vote.

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Obsessed or Hot Mess? Vote on These Daring Looks

THE BUST BAND

When we first saw this shot of Chrissy Teigen, we wondered if she'd actually stepped out in a totally sheer dress and some photo editor had added the black "censored" bar across her chest. But no, that's just how the dress is ... and we're pretty into it.

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Obsessed or Hot Mess? Vote on These Daring Looks

THE DÉCOLLETAGE TIE

If businessmen are so sick of wearing ties, perhaps they should consider doing as Selena Gomez (in Emilio Pucci) does and wear a sheer tie-shaped panel instead. Way sexier and has the added bonus of looking like an upside-down exclamation point.

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Obsessed or Hot Mess? Vote on These Daring Looks

BERMUDA SHORTS

There's a reason the jingle goes, "Who wears short-shorts?" and not, "Who wears conservative, knee-length shorts?" But Kourtney Kardashian chooses sensible over sexy in a white pair, then goes out on another style limb by adding a d.RA peplum top and a clutch that makes the word "oversize" seem like an understatement.

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Obsessed or Hot Mess? Vote on These Daring Looks

ROMPERS

Can you believe it's already time for the annual spring "Are onesies cute or or not?" debate? Well, we know where Alessandra Ambrósio, who wears a lacy blue Lover romper, stands on the matter.

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Obsessed or Hot Mess? Vote on These Daring Looks

THE SLIT-MEETS-SHEER-PANEL

January Jones wears a Jonathan Saunders dress and proves that two rights might very well make a wrong, combining a couple of trends we love (leg-baring slits and see-through detailing) to play peekaboo with her left leg.

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Obsessed or Hot Mess? Vote on These Daring Looks

FLAT BRIMS

For the record, we think Ashley Greene and every other woman can wear whatever they want to the gym, but we're really hoping Ashton Kutcher doesn't adopt this cap style for everyday wear and make it the next trucker hat.

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Obsessed or Hot Mess? Vote on These Daring Looks

MATCHING YOUR DRESS TO YOUR MAKEUP

There's already a verdict on matchy-matchy accessories, but what about this subtler form of coordination? Emmy Rossum complements her white-and-green Topshop dress with green eye shadow.

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Obsessed or Hot Mess? Vote on These Daring Looks

LIPSTICK SWEATERS

Wearing your heart on your sleeve: totally acceptable. But wearing your love of beauty products on your chest, as Mindy Kaling does? We'll let you decide.

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Obsessed or Hot Mess? Vote on These Daring Looks

COTTON-CANDY PINK

Grown women like Eva Mendes and Diane Kruger are sporting the shade typically reserved for newborn girls on their jackets, bags, jeans and flats.

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Obsessed or Hot Mess? Vote on These Daring Looks

GRECIAN JUMPSUITS

We think Nina Dobrev looks all kinds of hot in her formal one-shoulder Max Mara onesie, but we want your opinion on her gown-eschewing, drape-loving style.

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Obsessed or Hot Mess? Vote on These Daring Looks

CHRISTMAS COLORS IN MARCH

Here comes Santa Claus, here comes Santa Cl – oh, our bad. That's just Jessica Alba wearing a pair of chic army-green pants with a bright orange-red moto jacket.

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Obsessed or Hot Mess? Vote on These Daring Looks

TIE-DYE JEANS

We love jeans. We love tie-dye. So you'd think that we'd be very into LeAnna Rimes's James Jeans jeggings. And yet ...

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Obsessed or Hot Mess? Vote on These Daring Looks

BRAS AS FORMALWEAR

Remember the old days when you had to get just the right bra for your fancy dresses, often trying half a dozen before you found one that didn't show? Lea Michele declares that a waste of time and pairs visible lacy lingerie with a revealing gown.

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Obsessed or Hot Mess? Vote on These Daring Looks

JUMPSUITS

The King is alive! Oh, wait, that's just Camila McConaughey wearing an Elvis-inspired, bell-bottomed black onesie.

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Obsessed or Hot Mess? Vote on These Daring Looks

SWEATSHIRT DRESSES

Swap out Rihanna's skyscraper ankle-strap heels for a pair of L.A. Gear sneakers and this was almost the exact look we rocked back in fifth grade.

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Obsessed or Hot Mess? Vote on These Daring Looks

CARGO DRESSES

For those days when you can't decide between a dress and those cargo shorts you haven't worn in 10 years, we present to you this solution: the cargo dress, as seen on Rose McGowan.

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Obsessed or Hot Mess? Vote on These Daring Looks

KNEE-HIGH GLADIATORS

Sandal season is right around the corner, but we have a feeling you won't need to fight other women (to the death) to get your hands on a pair of these intricate lace-ups, seen on Rita Ora.

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Obsessed or Hot Mess? Vote on These Daring Looks

T-STRAP TOPS

Try to ignore, hard as it may be, the fact that her shirt has two tails blowing in the wind, and focus on Kim Kardashian's neckline, which reminds us a bit of a sports bra worn backwards.

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Obsessed or Hot Mess? Vote on These Daring Looks

SEQUIN PANTS

We knew we never should have gotten rid of our jazz recital costumes! Kelly Osbourne brings back the pants but wears them as we never did during our performances – with stacked pumps and a blazer and over nothing but a bra.

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Obsessed or Hot Mess? Vote on These Daring Looks

BEJEWELED TURTLENECKS

Sick of being relegated to the giveaway pile, turtlenecks finally have their moment in the sun, thanks to Nicole Kidman who forgoes a traditional cotton version and instead wears one covered in bling.

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Obsessed or Hot Mess? Vote on These Daring Looks

DEEP-V BLAZERS

There are ladies who lunch (wearing blouses under their blazers) and there are ladies who plunge (wearing nothing under their blazers). Jessica Biel and Selena Gomez fall into the latter category.

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Obsessed or Hot Mess? Vote on These Daring Looks

GIANT KEYHOLE CUTOUTS

Another star who clearly graduated with an advanced degree in Cleavage Display, Ashley Benson shows what she's working with in an Amit GT halter gown featuring a skin-baring design.

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Obsessed or Hot Mess? Vote on These Daring Looks

FURRY HATS

Somewhere a Halloween store is missing one of its '80s rocker wigs. They probably have no idea it's on Olivia Palermo's head at a Fashion Week show.

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Obsessed or Hot Mess? Vote on These Daring Looks

DRESSES OVER PANTS

We like Julianne Hough's floral Georges Hobeika Couture dress. We like the coordinating formal clamdiggers. We just don't know how we feel about the two together.

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Obsessed or Hot Mess? Vote on These Daring Looks

THE HORIZONTAL SLIT

Now that cutouts and thigh-grazing slits are as commonplace as skinny jeans, the unique way to show some skin on the red carpet is via this mid-leg slash, as seen on Marion Cotillard's Dior Haute Couture creation.

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Obsessed or Hot Mess? Vote on These Daring Looks

BLEACHED JEANS

The '90s were a good decade for Britney Spears (she starred on the All New Mickey Mouse Club and she released "… Baby One More Time"), so we can understand why she'd want to bring back that era, starting with her denim.

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Obsessed or Hot Mess? Vote on These Daring Looks

HANDKERCHIEF HEMS

You've seen it on maxidresses and beachy skirts, but Rooney Mara takes the typically casual hemline on the red carpet via her embroidered Valentino number.

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Obsessed or Hot Mess? Vote on These Daring Looks

FORMAL FUR

No Cookie Monsters were harmed in the making of Sarah Jessica Parker's Nonoo alpaca coat, but we're not sure if Lindsay Lohan's hooded white topper is as animal-friendly.

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Obsessed or Hot Mess? Vote on These Daring Looks

FOLDOVER PANTS

Wrap dresses: universally flattering. Their lesser-known cousin, wrap pants: not so much. (Unless, of course, you're the very petite, very fashion-forward Nicole Richie, in which case you can get away with wearing them.)

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Obsessed or Hot Mess? Vote on These Daring Looks

PURSE-ON-PURSE ACTION

It's gotta be nice to own so many amazing bags that you can't possibly tote just one. Jessica Alba must have that very awesome first world problem because she steps out with both a Gerard Darel handbag and a simple envelope crossbody.

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