Remember, a person’s entire body of work — from post-Oscars 2016 through the Oscars this year — is eligible. The photos we use aren’t the only ones you can use to decide. We’re finishing out Round One today; polls will be open for 24 hours, and Round Two will tip off next week. Happy voting!
(1) Rita Ora vs. (16) Kate Upton
Yesterday, we had one new judge from the rebooted ANTM, and today we have the host. However, while Ashley Graham wore some extremely questionable things on that program, she didn’t make sure the paparazzi photographed her traveling to and from work at every opportunity, whereas Rita made the pavement her runway. (Ashley, if you want a top seed — and you’re close! — you’re gonna have to take some notes from La Ora on How To Be Seen.)
I for sure remember Rita wearing this overtight “Oops I Did It Again” suit on ANTM. These boots look like they could have been a teach or a challenge just THEMSELVES. And she also wore this, but neglected to add her maracas. However, I have bleached from my brain whether this was for fun or profit:
For her sake, I hope both? I mean, it’s certainly fun for ME to see her dressed as Rainbow Brite’s mechanic.
That’s Marc Jacobs, and please, don’t let its hodge-podge heinousness distract you from the clodhopper poking out underneath. Rita actually loves a loud pattern, as with this Temperley thing, and the massive carpet she wore to a Fifty Shades premiere. She also wore a questionable DKNY suit that had a bunch of text on the back riffing on pronouncing that as a word, and I feel like… Donna Karan isn’t there anymore but if I were her, I’d have placed a VERY IRRITATED PHONE CALL about a jacket that’s all giggly about her long-established successful brand: “Tee hee, DICNY!!!”
NO. Everyone please just… stop doing these things to pants. Please. Except for you, Rita, because I guess see-through pants beats no pants at all:
Girl. Her Met Gala gown also had some obligatory side-butt, but this is a whole other league of WTF. (It might actually be the same Philipp Plein that Heidi Klum sported; Plein participated in ANTM this cycle.)
Kate Upton is here largely for this irritatingly coy full moon on her birthday.
Yes y’all are SO hilarious.
Kate’s crimes are mostly just fit related, or blandness, or fit-related blandness with a void of lipstick. Her placement at the bottom of the bracket is a combination of wah-waaaah moments and the Terribly Proud Of Herself starry Jenny Packham that showed off her rump floss. Although I did also find this in my research:
Is that… a bib made of industrial paper towels?
Selena was MIA for a lot of the eligibility period, but she crammed in a bunch of stuff right near the beginning, thanks in part to an association with Louis Vuitton that ultimately led her to wear a gown of theirs that comes with its own leather sports bra. And she did not resist one of its sheers, either:
At the time I fretted that she’s got a full-body sheer tulle poncho over an actual dress, and I still think it’s possible. What happened to elegance, LV?
This is Monse, being EXTREMELY Monsey. She also fell for the Mugler skin belt:
And… whatever this is:
The dress is terrible. But the shoes seal the envelope and mail it.
While Selena was taking chunks of the year off, Michelle Monaghan was stringing together possibly her worst year in memory. She has worn some questionable stuff in the name of fashion, y’all, and she can even go Skin Belt to Skin Belt with Selena.
Is the Vanity Fair Oscar Party really a time for side-abs? I mean, maybe. I’ve never been. I did stand outside one time, though, across the street (I used to live within walking distance of where they threw it). Michael Caine arrived in front of me, and then behind him pulled up John Rhys-Davies (Gimli in Lord of the Rings). He got out of his car and promptly freaked out that Michael Caine was nearby. It was great. Neither of them flashed any side-abs.
Michelle liked this Off-Whites dress so much, apparently, that she wore a different version of it to the CFDAs. That one isn’t great, but the above is worse — it hangs so low and the pleats look stapled onto the skirt. Terribly underwhelming. It’s deeply, deeply sub-whelming. As is this:
You’re killing me, Larry. Or Louis, as it were.
That’s Elie Saab, I think, and somehow she managed to make it even worse with the hairy shoes. I am not sure there’s much that could’ve been done to make this work; this dress actually IS interesting, but it needs to be cut off at the knee and possibly also tone down its own sleeves. Quite a few of her outfits tend to be a wee overdone, in fact, like this one that has too many ruffles.
I’m glad she’s laughing, at least.
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(5) Chrissy Teigen vs. (12) Gabrielle Union
Let’s start with what these two have in common: Each of them chose to wear something this year that challenged their waxers’ competencies.
Chrissy’s dress infamously terrified everyone at the AMAs, and was precarious in motion as well. Gabrielle won worst-dressed at the Oscars for her treacherous version:
Both ladies also wore hugely questionable white gowns:
This is legit terrible, but it’s possible Gabrielle’s is worse:
Chrissy’s other see-through white dress is mad unfortunate, too, and Gabrielle’s other contender in this arena made her look four times wider than she really is.
We also found some equally bad Going About Town clothes.
No. That top is MADE of no. As is this one. And yet:
I don’t even UNDERSTAND that top. Or the pants.
Craving a battle of black see-through gowns? I’m here for you.
I didn’t notice at first just HOW sheer this was because I got so distracted by all the strings.
Whereas parts of that almost look painted onto her body. (I also could have countered with this one, frankly.)
As fuller coverage goes, Chrissy went with a very ornate Marchesa at the Golden Globes, followed by this patchy mess at the Oscars:
Gabrielle, meanwhile, went with an unwelcome bonus bra, and then this stiffly dramatic confection:
(8) Kristen Stewart vs. (9) Cara Delevingne
Kristen has had an up and down year. She wore some okay suits, but then ended up in satiny warmups. She seemingly got better at wearing high heels to things, but hosted SNL wearing an artist’s rendering of my IKEA mesh-metal wastebasket. She experimented with various hair colors, but temporarily had her legs erased by a weird optical illusion. And then she had to wear these at Cannes:
She has a habit of overdoing eyeshadow, and I tend to think it dovetails with when she’s super tired. But drawing MORE attention to the eyes is not much help. Wearing semi-winged sleeves actually distracted me more.
Pockets are the new bras?
Exactly how many safety-pin emergencies does she expect to get into today?!? And couldn’t she have used ONE of those to attach the other sleeve to her shirt?
And this… I think Kristen Stewart has shown flashes of more interesting taste than this mess would indicate, which just makes it worse and lazier to me.
Cara Delevingne, being a successful model, does have the capability to pull off things that would be absurd on most people. Although the longer I look at it, the more I agree with Fug Nation that this weird green satin cape dress looks like it cost $10.
Imagine that hair and makeup on an actual garment! Oh, what could have been.
Not even Cara can convince me this whole thing wasn’t totally overwhelming. And what about THIS one:
That SCREAMS for slightly different choices. You had a good fabric! It works with the leather! But the garment hanging way too loud a bell on the design. All I can see is the pieces and not the whole.
This feels like a craft project.
And I need someone to explain to me what that neck string is doing. It makes her head look like it’s on backward and/or that her entire skin can be zipped on and off.
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