As a refresher: The photos and links in each matchup are NOT the only outfits eligible; rather, they’re a representative sample of the body of work. Polls close after 24 hours, so if you like to research your choices — on our site, Getty Images, Google, whatever — have at it and just make sure you vote before the game ends. Enjoy.
(2) KIM KARDASHIAN vs (15) LIBERTY ROSS
For a while, we were discussing having Pregnant Kim Kardashian play Nonpregnant Kim Kardashian in the play-in game, but we realized BOTH iterations of KimKard deserved to be seeded MUCH MUCH higher than 16. She BROUGHT THE FUG MADNESS THIS YEAR. I mean, do you remember THIS? You will never forget it once you revisit it. I’m serious. We could NEVER forget these BIZARRO PANTS. Nor this halter/jumpsuit (humpsuit? No, wait. That’s something else. DON’T WEAR THAT).
And this is likewise distressingly weird:
Why does so much of Kim’s wardrobe involve an animal or something that makes her look like she’s turning INTO an animal? This has a tail, for example, and I’m pretty sure it sheds:
I think this…vest? Jacket? Shrug? Capelet? … is either made of Westminster Dog Show champion or an actual kitchen mop. Get ready for it to hit you in the face:
This is the fireside rug on which Blake Carrington once made sweet love to Krystal as a way of distracting her from the fact that he sent his Gay Son off to get blown up on an oil rig and return with a whole new face after killing said Son’s Lover by kind of sort of accidentally cracking him on the head:
Even Kanye is skeptical of whatever is happening with this poor creature:
Do you really want KANYE WEST wondering what you’re wearing? NO. NO YOU DO NOT.
Speaking of awkward:
In retrospect, the truth about Kristen Stewart and Rupert Sanders is written all over K Stew’s face there. Liberty Ross’s dress looks lovely from the side, but from the front it’s clear she got infected by the Sheeritis that ran through that cast like swine flu:
If that were lined, I think we’d all be singing a different tune. In fact, Ross never lines anything. Behold her Oscar frock:
She and Kim K actually also crossed paths at the Topshop opening here in Los Angeles. If Kim was wrapped up in the feathers of the ancient dodo, or whatever it is she was molting, Liberty was once again nip-adjacent:
I’m sure she is going through a lot right now — if she and Sanders are divorcing, she may well be trying to rustle up the PR so she can get work again and make some money for herself and her kids –but nipples are hardly EVER the answer.
(3) CARLY RAE JEPSEN vs. (14) SARAH JESSICA PARKER
The battle of the three-initialed ladies! Let’s start with CRJ:
Why is everyone in this bracket wearing an animal?
Here, it seems apt that She Who Will Not Dress Her Age (27…which it has been for over a year, I believe) is wearing something fun-sized to a movie by the same name:
And this romper is even smaller than fun-sized, if there is such a thing. It’s more of an amuse bouche of an outfit than an actual meal:
I worry that she can’t actually stand up in it without something popping out. Also, again, she is a year older than Lady Gaga. Just…percolate on that for a little bit. She’s lucky her face is so very young, but they’ve GOT to start aging this girl’s style up a little bit or things are going to get awkward. As in many things: Look to Madonna. At least, look to Madonna between 1985 and 1998.
I literally don’t even know what this IS, other than a bad idea:
This, though, I can easily ID. It is a schoolgirl’s uniform:
Say what you will about SJP, but she’s not going to show up dressed like a Catholic schoolgirl. Well, not if it’s not required by Sex and the City 3D. In fact, I’d argue that she spend this Fug Madness period of eligibility dressed OLDER than she actually is (47):
I mean, at least that dress is AIRY. It’s totally Cocktails on the Lanai With Blanche, which I completely endorse IF YOU ARE HAVING COCKTAILS ON THE LANAI WITH BLANCHE. But airy is better — arguably, anyway — than musty:
I hope she saved this because she’s going to look amazing in it when she’s 85. Ditto the following, which was possibly my LEAST FAVORITE dress of all Fug Madness eligible looks:
It turns out that I am really really really not into Valentino lately, primarily because I don’t want to wear the inside of a Crabtree & Evelyn on my body. This is equally musty (though I love the gardenia on her lapel, both because gardenias are lovely and because the tiny shout-out to Carrie Bradshaw is sweet):
Uh, at least James Wilkie looks smart? And speaking of shout-outs to Carrie Bradshaw, does anything scream SATC like Bradshaw sporting a visible bra during a moment when no bra ought to be visible?
(6) CATE BLANCHETT vs. (11) HALLE BERRY
I predict this will be a close match. Because we’ve got Carte Blanchett – who gets away with things because she’s Cool Collected Cate Blanchett and she seems awesome and wise and confident and groovy — versus Halle Berry, who often gets a pass thanks to being The Tremendously Gorgeous Halle Berry. Two women whose looks we WANT to love enter the ring. ONLY ONE WILL LEAVE.
Let’s kick it off with Cate:
That looks like a Project Runway challenge. Those sleeves ARE made of Hefty bags, and you can totally just wipe them down, like a plastic picnic tablecloth, and the hem is stapled. CATE BLANCHETT, you are CATE BLANCHETT. Your skirts should be hemmed by the power of your MIND.
This ALSO looked like student work to me:
Her bob is adorable, but the middle of this dress looks like a special Hanes diffusion line for Spanx. Hanes for Spanx. Hanx.
This is another mash-up, of a shirt and a poncho. It’s a shoncho:
AND THIS IS A ROMPER. CATE BLANCHETT YOU DON’T WEAR A ROMPER. DON’T EVER WEAR A ROMPER AGAIN:
I need to lay down, but first we need to talk about Halle Berry and how she’s trying so hard lately and how silly that is because SHE IS HALLE BERRY:
This is TMI and I used to be pretty sure we’d never get TMI from Halle Berry. How MI is T with someone so gorgeous? Now we know.
Then there’s her habit of dressing like Prince:
Even Prince is all, “I don’t know, babe.” And then there are these pants, a blight against the world and a constant object of horror for me personally:
And this? It’s just perplexing:
I plan to just focus on both of their faces from here on out. But while you’re doing that, VOTE IT UP:
(7) KEVIN McHALE vs. (10) EMMA ROBERTS
I am pretty excited about Kevin McHale’s potential Fug Madness run. I think he could be the Ryan Cabrera of this year, with less intense hair and probably fewer nipples. I also actually am kind of into this, although I can admit at the same time that is is INSANE and he should be playing the Poconos in it:
But at least that green suit is not giving me a seizure, while this combo may well do so if I don’t scroll down, like, REAL fast:
I legitimately don’t even know what this is, although I think the shoes are groovy (and overall, I salute the dude for having a point of view; so much men’s wear is BOOOOOORING and he’s admirably interesting, at least):
THIS is straight from a direct to DVD sci-fi movie where people fall in love with holograms and someone gets eaten by a two-headed snake:
And these PANTS are the cheesy BACKGROUND of that sci-fi movie:
But are space-printed pants enough to take down….whatever this is? I mean, I know Emma Roberts here is from Coachella, but…ELLIPSIS. ELLIPSIS ELLIPSIS.
I feel like someone told Emma Roberts that Coachella is a pool party (it is not), or that this is a dress (also not):
It’s telling when pants not seen since I last walked past a bunch of stoners playing hackysack at UCLA in front of the Taco Bell in 1995 are the most acceptable vacation outfit, and what it tells us is, GIRL. LEARN TO PACK FOR A WEEKEND BETTER THIS YEAR:
Emma had a couple of missteps on the red carpet, too — namely, this. Which is ALSO undergarment-y:
I did, however, forget that she’s dating Evan Peters, who looks super sharp. At they’re batting .500 at this one.