Obsessed or Hot Mess? Vote on These Daring Looks

FANCY HOODIES

Ciara's yellow beaded Emilio Pucci mini-meets-hoodie is way more versatile than it appears. She can wear it over a bikini while hanging on some billionaire's yacht or in the boxing ring should she ever consider a second career.

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Obsessed or Hot Mess? Vote on These Daring Looks

SUPER WIDE-LEG PANTS

We can only imagine the enormous gust of wind Olivia Wilde must generate just by walking in these oversize pleated Michael Kors pants (worn with a blouse owned by every elementary school librarian).

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Obsessed or Hot Mess? Vote on These Daring Looks

LACE SLASHES

The best (or worst) part of Emma Roberts's T-shirt is that you know she paid extra for those lace-covered holes.

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Obsessed or Hot Mess? Vote on These Daring Looks

SERIOUSLY OVERSIZE CLUTCHES

We look for an evening bag roomy enough for keys, credit card, lipstick and iPhone. Christina Hendricks, though, seems to look for one that'll fit a MacBook Air.

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Obsessed or Hot Mess? Vote on These Daring Looks

LABEL BELTS

Consider Kourtney Kardashian's Moschino belt the haute equivalent of a "Hi My Name Is ___" sticker name tag.

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Obsessed or Hot Mess? Vote on These Daring Looks

AVIATOR GLASSES

We know who swiped Bobs' spectacles from the Office Space prop closet: Jennifer Aniston, who wears them 15 years later.

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Obsessed or Hot Mess? Vote on These Daring Looks

HEART-PRINT TIGHTS

The last time we wore tights like this, we were closer to Suri Cruise's age than Katie Holmes's age. (And the heart tights we wore were white, opaque and matched our patent-leather Mary Jane flats.)

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Obsessed or Hot Mess? Vote on These Daring Looks

CAPES

Always wondered what to pack for a weekend of pheasant shooting in Scotland? If you're Pippa Middleton you bring a wool, camel-colored coat-cape.

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Obsessed or Hot Mess? Vote on These Daring Looks

FLANNELS AROUND THE WAIST

First overalls. Then crop tops. Now the straight-outta-the-'90s plaid button-down tied at the midsection (seen on Lily Collins). Next you'll be telling us that Saved by the Bell is back on the air.

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Obsessed or Hot Mess? Vote on These Daring Looks

COMIC BOOK DETAILS ON GOWNS

Pow! Ka-bam! Zap! One of those statements is all that's missing from the sequin explosion motif on Rita Wilson's Tom Ford dress.

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Obsessed or Hot Mess? Vote on These Daring Looks

TUTU PEPLUMS

Do you think Sarah Michelle Gellar's daughter is annoyed that her mom took this girlie ballerina skirt out of her dress up trunk and wore it to a TV appearance?

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Obsessed or Hot Mess? Vote on These Daring Looks

THE IS-IT-A-BRA-OR-IS-IT-PART-OF-HER-DRESS DRESS

We were originally concerned that Diane Kruger was having a wardrobe malfunction and accidentally showing her undergarments. But it turns out that's how the Jonathan Saunders dress was designed.

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Obsessed or Hot Mess? Vote on These Daring Looks

MULLET TEES

If you've been spending all your time at the gym doing crunches, but skipping the squats, consider this high-low crop top, which shows off your abs and covers your butt. (Not that Holland Roland needs to be concealing any part of her perfect body.)

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Obsessed or Hot Mess? Vote on These Daring Looks

BUTTERFLY PRINTS

Are Miranda Kerr's Lanvin pants uniquely chic or is the pattern best left to girls who are still using Lisa Frank school supplies?

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Obsessed or Hot Mess? Vote on These Daring Looks

CROPPED TUXEDOS

When we think of belly showing between pleated pants and a double-breasted blazer, we think of middle-aged men trying to squeeze into the same suit they wore in their early 20s. The look on model Anne V, however, is much more chic.

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Obsessed or Hot Mess? Vote on These Daring Looks

THE JEWELED SIDE CHAIN

Skater boys who wear their wallets on chains connected to their jeans are wondering why Kate Bosworth is copping their style. Of course, her outfit is Thakoon, not JNCO, and it's purely for looks since her publicist is probably carrying her wallet.

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Obsessed or Hot Mess? Vote on These Daring Looks

EXTRA-LONG BLOUSE NECK TIES

If the ties are so long that you wouldn't get on an escalator for fear that they'd get caught in the side, they're probably too long. You listening, Mena Suvari and Mischa Barton?

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Obsessed or Hot Mess? Vote on These Daring Looks

THIGH-HIGH STOCKINGS

Move over, sexy schoolgirl costumes and exotic dancers! Katy Perry is stealing your over-the-knee accessory and making it her own.

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Obsessed or Hot Mess? Vote on These Daring Looks

ARMPIT CUTOUTS

Sweat stains are a problem of the past thanks to gowns like Coco Rocha's Greta Constantine one. We're so glad a designer finally created a dress that addresses that very real issue.

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Obsessed or Hot Mess? Vote on These Daring Looks

METAL SHOULDER PADS

It's almost as if a medieval warrior and one of the Designing Women got together and crafted this look, worn by Shay Mitchell.

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Obsessed or Hot Mess? Vote on These Daring Looks

HEISENBERG HATS

Bad things happen when Walter White puts on this topper, but does Jessica Alba slipping it on make you as nervous?

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Obsessed or Hot Mess? Vote on These Daring Looks

FUR CROP TOPS

For those days when it's cold enough for a winter coat, but you think your body is smokin' hot enough to share with the world: a belly-baring topper like Sienna Miller's Burberry one.

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Obsessed or Hot Mess? Vote on These Daring Looks

MINI BRIEFCASES

In movies, this kind of carryall is usually filled with stacks of cash or important legal papers. But we don't see how Jessica Biel could fit either in this tiny Mark Cross bag.

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Obsessed or Hot Mess? Vote on These Daring Looks

THE ASYMMETRICAL FLY

Heidi Klum, XYZ. As in, examine your zipper. That's exactly what we're doing since we're so intrigued by the diagonal closure on her cropped black pants.

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Obsessed or Hot Mess? Vote on These Daring Looks

DOUBLE-HANKY SKIRTS

Have a runny nose? Maybe Ashley Tisdale will lend you half of her Chaser skirt, which reminds us of two handkerchiefs fastened together.

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Obsessed or Hot Mess? Vote on These Daring Looks

INSANELY OVERSIZE HOOPS

We've won hula hoop competitions with hoops smaller than the ones in Rihanna's lobes. But we'll let you decide whether her earrings are winning or not.

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Obsessed or Hot Mess? Vote on These Daring Looks

CROPPED SWEATERS

And here we were worried that we'd have to go the whole winter without seeing a single crop top. Our fears were unfounded, though, because Pink has found a cozy knit version of the popular style, which can be worn even when temps drop.

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Obsessed or Hot Mess? Vote on These Daring Looks

CORD OVERALLS

If denim overalls are starting to feel so 15-minutes-ago (you know, in addition to so 15-years-ago), allow us to suggest the latest update of the onesie: the corduroy style like Bella Thorne is wearing.

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Obsessed or Hot Mess? Vote on These Daring Looks

NEWSBOY CAPS

Would we love for Channing Tatum or Leonardo DiCaprio to deliver the newspaper to our house every morning? Hell yes. Would we like for them to do it in their patterned wool toppers? Debatable.

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Obsessed or Hot Mess? Vote on These Daring Looks

PEASANT DRESSES

Yes, it's Gucci. And yes, Miranda Kerr is wearing it with Chanel sandals and a Valentino bag, but does anyone else get a cover-of-a-romance-novel vibe from the supermodel's blue silk off-the-shoulder peasant dress?

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Obsessed or Hot Mess? Vote on These Daring Looks

DIAMOND CHOKERS

Normally this type of necklace reminds us of a bedazzled dog collar, but even Paris Hilton's chihuahua Tinkerbell never wore anything as blinged-out as the styles Rihanna and Jennifer Hudson have on.

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Obsessed or Hot Mess? Vote on These Daring Looks

OVER-THE-TOP RUCHING

When we can't figure out how to fold a fitted sheet, we just ball it up and put it in the closet. Stacy Keibler, however, gets creative and fashions it into a one-shoulder dress.

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Obsessed or Hot Mess? Vote on These Daring Looks

VISIBLE POCKETS

Maybe we're turning into our mom, who wouldn't let us wear shorts like this back in middle school, but we think Vanessa Hudgens's cutoffs with their peek-a-boo pockets are best left at the mall. Cute hat, though.

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Obsessed or Hot Mess? Vote on These Daring Looks

XXL SHIRTS

Maybe Lily Collins accidentally wandered into the Big & Tall section where she picked up this mega-oversize shirt that's practically falling off her petite frame.

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Obsessed or Hot Mess? Vote on These Daring Looks

LUCITE HEELS

Once the sole domain of a certain type of dancer, these plastic-soled shoes have migrated onto the feet of women in slightly less, uh, exotic industries, like Lady Gaga, who wears a Ruthie Davis pair.

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Obsessed or Hot Mess? Vote on These Daring Looks

FINGERLESS GLOVES AS FORMALWEAR

It's not about being able to text when it's cold out. It's not about getting a good grip on the steering wheel in the winter. It's about ... actually, we have no idea what Kourtney Kardashian's striped cutoff gloves are about.

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Obsessed or Hot Mess? Vote on These Daring Looks

CORSET-STYLE BELTS

Back in the 16th century, women wore corsets under clothing, but we've come a long way, baby. Because now stars like Jennifer Aniston are wearing them over their clothing as accessories.

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Obsessed or Hot Mess? Vote on These Daring Looks

THE BUTT RUFFLE

Well, it's official. After seeing Lily Collins's Stella McCartney mini with it's three-quarter peplum, we'll be singing "Ruffle butt, ruffle-ruffle-ruffle butt" to the tune of "Bubble Butt."

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Obsessed or Hot Mess? Vote on These Daring Looks

THE SHEER STRIPE

We all (Rose McGowan included, apparently) know that knees are the most annoying part of the leg to shave. Which is why this Topshop skirt that shows off the calves and some thigh but hides the knee is so genius.

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Obsessed or Hot Mess? Vote on These Daring Looks

DRESSING LIKE A ZEBRA

We've always thought of Rihanna as more of a chameleon, but in this wild Tom Ford dress, complete with spiky fur at the neck, meant to look like a mane, the singer makes it clear her spirit animal is a zebra.

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Obsessed or Hot Mess? Vote on These Daring Looks

BATHING SUITS WITH SLEEVES

A hybrid of the one-piece and the surf rash guard, Olivia Palermo's Lisa Maria Fernandez swimsuit reminds us a bit of the leotards we used to wear for our ballet recitals (without the sexy zipper, of course).

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Obsessed or Hot Mess? Vote on These Daring Looks

DOUBLE-WIDE TIES

If a clown were in mourning, we imagine he'd wear a short, fat tie like the black one Amanda Seyfried dons around her neck.

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Obsessed or Hot Mess? Vote on These Daring Looks

UNDERWEAR-BARING JEANS

Hey, boys do it all the time, so why shouldn't women have equal opportunities to show off their skivvies with low-slung pants? Shailene Woodley and Kristen Stewart fight for this very important right.

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Obsessed or Hot Mess? Vote on These Daring Looks

COLLARED CROP TOPS

"You can't go wrong with a collared shirt for a job interview," said the career counselor who never saw this Roland Mouret version of the blouse, spotted on Lily Collins.

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Obsessed or Hot Mess? Vote on These Daring Looks

MANBANDS

Guy hair don't care. Colin Farrell isn't one to follow gender style stereotypes, wearing a stretchy headband, not to mention earrings, bracelets and a hevage-revealing shirt.

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Obsessed or Hot Mess? Vote on These Daring Looks

SHOULDER PADS

Working girls Julianne Hough and Heidi Klum look ready to rule the boardroom and order the business woman's special in their strong-shouldered styles.

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Obsessed or Hot Mess? Vote on These Daring Looks

ACID-WASH JEANS

Another '80s trend making a comeback: mottled denim. Next time we accidentally drop our jeans in a bleach load, we plan to say it wasn't an accident and wear them as Kate Hudson does.

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Obsessed or Hot Mess? Vote on These Daring Looks

MEN'S DRESS SHOES ... ON WOMEN

That is not a zoot suit Nicole Richie has on (we're actually not sure what to call the separates she has on), but her two-tone Saint Laurent brogues are certainly zoot suit compliant.

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Obsessed or Hot Mess? Vote on These Daring Looks

CLEAR PLASTIC PENCIL SKIRTS

Your HR manager called. She'd like to rescind her previous comment that you can't go wrong with a below-the-knee skirt and a button-down. Good thing Rita Ora, in Burberry Prorsum, doesn't have a traditional 9-to-5.

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Obsessed or Hot Mess? Vote on These Daring Looks

PRETTY WOMAN BOOTS

Would you call these over-the-knee stilettos "a big mistake, big, huge" or do you love Lily Collins's sexy footwear?

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Obsessed or Hot Mess? Vote on These Daring Looks

EMPIRE WAIST TURTLENECK DRESSES

True story: We had an impromptu mini-meeting to figure out what to call the two-tone number Britney Spears is wearing. In California, in August, we might add.

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Obsessed or Hot Mess? Vote on These Daring Looks

DREAM CATCHER NECKLACES

Remember those woven hoops decorated with feathers and beads that you hung over your bed? Evidently Shailene Woodley does, since she recycled it as a rather unique red carpet accessory.

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Obsessed or Hot Mess? Vote on These Daring Looks

SHREDDED HEMS

It's almost as if Emilia Clarke wanted to destroy the evidence of her top then thought better of it halfway through.

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Obsessed or Hot Mess? Vote on These Daring Looks

SKELETON LOAFERS

If you thought getting an X-ray was expensive, just consider Julianne Hough's X-ray flats, which go for $350.

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Obsessed or Hot Mess? Vote on These Daring Looks

LEATHER BERMUDA SHORTS

Knee-length denim shorts got your seal of approval, but baggy did not, so we can't even begin to predict how you'll feel about Rita Ora's look here.

Obsessed or Hot Mess? Vote on These Daring Looks55 of 56 - Credit: Wolff/INF