Obsessed or Hot Mess?

THE ULTRA-FLUFFY PURSE

Has Beyoncé found the most glam way to tote warm leftovers … ever? It would be one explanation for why she'd need to carry a purse (hers is Dee Ocleppo) covered with a thick layer of fur.

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Obsessed or Hot Mess?

THE MISMATCHED BUTTON

Keira Knightley's top has "got dressed in the dark" written all over it thanks to the misaligned lace placket. But since it's a fancy designer, we have to assume it was meant to look that way.

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Obsessed or Hot Mess?

THE SIDE-CUTOUT SKIRT

Celebs have been coming up with creative new ways to show skin recently, and Nicole Scherzinger's body-con look may have topped them all. She somehow squeezed three thigh cutouts into a tiny miniskirt.

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Obsessed or Hot Mess?

LADYLIKE BOWLER HATS

Taylor Swift has been wearing these itty-bitty bowlers for quite some time, but now that we see her step out in style almost every day we've got to put it to a vote: Is her favorite look haute hipster, or Charlie-Chaplin-cheesy?

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Obsessed or Hot Mess?

THE CHAMBRAY TURTLENECK

Bored of your wear-it-everywhere denim button-down? Are you bored enough of it to consider a jean crop top like Kylie Jenner's One x One Teaspoon number?

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Obsessed or Hot Mess?

GIGANTIC CUTOFF JEANS

There are wide-leg jeans, and then there are Rihanna's wide-leg jeans, which evoke JNCO jeans of years past more than any others we've seen thanks to the ultra-frayed hem and waistband.

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Obsessed or Hot Mess?

FLUFF-TRIMMED FROCKS

It's one part can-can dancer, one part sassy nightie, with a hefty twist of Black Swan. No wonder Alexa Chung couldn't resist this Simone Rocha frock (she called it "a beautiful dream dream dress!").

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Obsessed or Hot Mess?

SUSPENDERS AND CROP TOPS

Taylor Swift has been pushing crop top boundaries since early 2014 – but has one of our Best Dressed stars gone too far with her dorky-chic suspenders and horse sweater?

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Obsessed or Hot Mess?

VARSITY JACKETS OVER GOWNS

It probably did get a little chilly after the Mockingjay London premiere, so we don't blame Jena Malone for needing a coat. But we think this stunning Emilia Wickstead dress deserves a slightly more formal cover-up.

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Obsessed or Hot Mess?

THE HIGH-FASHION SNUGGIE

Rihanna is wearing this DKNY sweatsuit to the airport and there's absolutely no question that it would be beyond comfy on a plane. But can we break our "No Snuggies in Public" policy just because it's Rih?

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Obsessed or Hot Mess?

NEXT-GENERATION HAREM JEANS

Gwen Stefani's pants are the natural evolution from the ultra-baggy pair Jennifer Aniston wore back in 2012, boasting a skinnier, more tapered leg and (somehow this is possible) an even deeper drop crotch.

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Obsessed or Hot Mess?

WHITE TIGHTS

We've long considered matching your tights to your heels (à la Zooey Deschanel) an instant leg-lengthener, but does the effect translate if you've picked alabaster stockings and pumps like Aubrey Plaza?

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Obsessed or Hot Mess?

THE INFORMAL COATDRESS

We've seen a few fancy jackets that double as dresses (Kate Middleton is a fan of the style), but we can't say we've seen one in a swishy, almost athletic material like Khloé Kardashian's Herman number.

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Obsessed or Hot Mess?

A NEW TAKE ON THE SWEATER SET

Light-colored ribbed turtleneck dresses are pretty unforgiving, even if you're as fit as Rihanna, but the singer throws us a major curveball (and curve-enhancer) by layering coordinating pants– not slimming tights – under hers.

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Obsessed or Hot Mess?

WEARING YOUR DRESS AS A SHIRT

You know those times when you desperately need to do laundry and have to dig deep in your closet for a clean button-down? Maybe Reese Witherspoon couldn’t find one so she just tucked her Tory Burch dress into her Misha Nonoo mini skirt instead.

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Obsessed or Hot Mess?

HOODIES WITH CAT EARS

Aw, Ariana Grande is all grown up! Never mind, that's Khloé Kardashian, giving her airport look a little feline flair.

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Obsessed or Hot Mess?

OVER-THE-KNEE BOOTS AND CUTOFFS

There's always a wee bit of danger that your thigh-high boots can read a little too Pretty Woman, but we're not sure Ashley Tisdale is helping her case by pairing her lace-ups with short shorts.

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Obsessed or Hot Mess?

PLAID-ON-PLAID SCARVES

It's hard to tell if Karolina Kurkova is wearing two scarves or just one reversible piece, but it's clear that while this two-toned tartan might not be for everyone, it's perfect for the indecisive.

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Obsessed or Hot Mess?

JAILHOUSE-STRIPE MAXI

People say things are "black and white" to indicate that they're very clear. And in this case, it's quite evident that the wide-striped two-tone pattern on Kristin Cavallari's body con dress may be tricky for more than one specific body type.

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Obsessed or Hot Mess?

LONG SHORTS SUITS

We've been impressed by nearly-business-appropriate shorts before, but something about the hemline of Jordana Brewster's pair (which falls somewhere between Bermudas and Beyoncé) is throwing us off here.

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Obsessed or Hot Mess?

THE SKULL-PRINT PONCHO

When was the last time you were spooked by a shawl top? It's been a little while since we've seen the once-hot skeleton motif out in the wild, but is Jewel's version helping it make a (comfy) comeback?

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Obsessed or Hot Mess?

TOTALLY MISMATCHED EARRINGS

We've all tried on different earrings in each ear trying to figure out which one goes best with our look. But was AnnaSophia Robb so indecisive she walked out the door with this combo (one Renee Sheppard, one Pearl Collective)? More likely she's going for a stud version of the now-ubiquitous solo dangler.

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Obsessed or Hot Mess?

THE SO-SHEER-IT'S-CLEAR HEM

Want to add some length to your LBD without sacrificing sexiness? Look no further than the plexiglass-style lining of Poppy Delevigne's dress, which is the most, well, solid spin on the extreme cutout trend we've seen thus far.

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Obsessed or Hot Mess?

SHAG RUG COATS

We have a lot of questions about Olivia Wilde's jacket, but at the top of that list: When she spills something on it, does she send it to the dry cleaner or just call Stanley Steemer?

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Obsessed or Hot Mess?

SILKY DUSTER ROBES

Some women prefer to dress like the Playboy bunnies. Not Lily Aldridge, though – she channels Hugh Hefner, swathing herself in a robe seemingly inspired by his.

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Obsessed or Hot Mess?

THE PANELED CUTOUT

We know Jena Malone's dress was designed to look like this, but it also prompts us to think that if we ever put on something with a cutout that makes us feel self-conscious, we can just add on some multicolored electrical tape to cover up part of the cutout.

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Obsessed or Hot Mess?

LEATHER OVERALLS

OshKosh B'Oh My Gosh. Olympic athlete Lolo Jones's onesie might be the farthest cry from the cute denim overalls we all wore as little kids.

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Obsessed or Hot Mess?

MAJOR FRINGE HEMLINES

We already knew Olivia Palermo had a degree in wearing fringe (evidence here). And after seeing this look, we now know she has a PhD in the trend.

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Obsessed or Hot Mess?

WIDE-LEG OVERALLS

Is Rita Ora's denim Stella McCartney onesie giving anyone else flashbacks to the era of JNCO Jeans? And does anyone else feel like maybe that's not such a terrible era to return to?

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Obsessed or Hot Mess?

FLUFFY PURSE CHARMS

If you've been waiting with bated breath for the return of Furbies (you have, haven't you?), you can finally let out a sigh of relief. Because Kendall Jenner has a fuzzy accoutrement seemingly inspired by the late-'90s trend, clipped to her Céline bag.

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Obsessed or Hot Mess?

KHAKI CULOTTES

Isn't it such a bummer when your office's "business attire" dress code gets in the way of you wearing your favorite wide-leg clam diggers? Luckily, the pants now come in corporate-friendly khaki (seen on Kaitlyn Dever).

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Obsessed or Hot Mess?

SLEEVELESS TRENCHES

The double-breasted, knee-length vest Nicole Scherzinger is sporting is either the ultimate transitional in-between-seasons piece or the most impractical raincoat ever.

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Obsessed or Hot Mess?

THE SINGLE HOOP EARRING

When Coco Chanel said, "Before leaving the house, a lady should look in the mirror and remove one accessory," we have a feeling she wasn't referring to one of your earrings. And yet, Lena Dunham followed the icon's advice and ditched a hoop.

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Obsessed or Hot Mess?

A FULLY FEATHERED PURSE

Does Jessica Simpson's avian accessory take wing and soar for you, or would you rather see this look permanently grounded?

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Obsessed or Hot Mess?

RACERFRONT LEATHER OVERALLS

Kristen Stewart has been on a major mini streak, which includes this seemingly lederhosen-inspired overalls skirt. She's lucky it comes with a shirt attached, because we can't figure out what bra would go best with this particular cut.

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Obsessed or Hot Mess?

DOG COLLAR CHOKERS

Apparently, if you're a bold brunette singer looking to make a statement, you're reaching way back to the '90s for a goth-inspired dog collar choker complete with leash clasp at the front of the neck. (Additional edgy jewelry optional, though Katy Perry and Jessie J. both went for it.)

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Obsessed or Hot Mess?

TAN HOSE AS PANTS

We've said it before and we'll say it again: Leggings are not pants. We just didn't realize we had to expand that statement to include nude pantyhose, which, despite having the word "pant" in the name, are a questionable bottoms choice (as seen on Ariana Grande).

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Obsessed or Hot Mess?

CAMPFIRE-CHIC ATTIRE

We wonder what's harder to pull off: looking like you belted a blanket to wear as a dress (à la Hilary Rhoda) or engaging in a three-way fashion face-off with Blake Lively on the cover of Vogue and the mannequin behind you.

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Obsessed or Hot Mess?

JUMPSUITS TIED AT THE WAIST

You might be asking yourself, Why wear a onesie at all if you're just going to wear it half-off? You might also be asking yourself, Could Rihanna be any cooler? Both would be valid questions.

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Obsessed or Hot Mess?

SWEATS WITH A MESSAGE

Does the graphic on Sarah Jessica Parker's pants adequately represent your feelings for her look or would you have gone with a different, not-so-happy emoji?

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Obsessed or Hot Mess?

SHEER PANTS OVER SHORTS

If you ask us, Cara Delevingne's plunging neckline isn't the craziest part of this jumpsuit (Kim Kardashian has raised our tolerance for major cleavage). It's the striped see-through flares layered over booty shorts that really grab our attention.

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Obsessed or Hot Mess?

SUPER-OVERSIZE SHIRTDRESSES

For those of you who feel that muumuus are just a tad too casual, Naomi Watts presents to you the collared formal version of the billowy design.

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Obsessed or Hot Mess?

BOOT-CUT BOOTS

We've already got fitted knee-highs, but after seeing this photo of Chrissy Teigen, suddenly we're considering investing in this bell-bottom style.

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Obsessed or Hot Mess?

TEES WITH PRINTED LEIS

Hey, we want to be in Hawaii as much as Jessica Alba does (seen here in a Cynthia Rowley tee), but we're not sure we'd take our vacay fever to this extreme. (P.S. How proud are you of us that we got through that whole caption with a "getting lei'd" joke?)

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Obsessed or Hot Mess?

SPANDEX CAPRIS OUTSIDE THE GYM

Would we ever wear the same stretchy pants we use for barre classes for a formal event? Unlikely. Then again, the stretchy pants we own are designer Alaïa leggings (like the ones Kim Kardashian has on).

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Obsessed or Hot Mess?

PLAID-ON-PLAID

Our biggest concern when wearing the tartan print is avoiding looking like a schoolgirl in uniform or an extra in Braveheart. We'd say that Jessica Simpson doesn't have to worry about being mistaken for either of those two things.

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Obsessed or Hot Mess?

STATEMENT NECKLACES OVER TURTLENECKS

Remember when everyone was wearing bling over their collared button-downs? Leave it to Olivia Palermo, Trendsetter Extraordinaire, to take the combo to the next level.

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Obsessed or Hot Mess?

HIGH-FASHION FANNY PACKS

We admit it, the idea of not having to carry a purse is pretty alluring. But so alluring that we'd adorn our waist with a Chanel carryall like Sarah Jessica Parker's? We may just stick to carrying our bags.

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Obsessed or Hot Mess?

BELTING YOUR SCARF

Whatever Olivia Palermo does style-wise, we often want to do it, too. Which is why we're not quite ready to write off her atypical accessories layering technique.

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