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.
(1) RITA ORA vs. (16) ADRIENNE BAILON
It may be her most infamous outfit — we, in fact, put it in People’s annual best/worst issue back in September — but in the past year Adrienne Bailon wore more than just a vagkin (my new, hopefully forthwith unnecessary term for vagina napkin). Not always MUCH more, in terms of volume, but more. In fact, as I mentioned in the play-in post, I’ve developed a theory that she’s DEVASTATED she is not a blood Kardashian, and is therefore trying to mold herself into a blonde Kim. Every picture I see cements that. Behold:
Am I right? If I told you this was a photo from that week when Kim decided to go blonde, or wear a wig, or whatever, you might believe me. This one is also particularly Kim-ish.
Okay, maybe Kim wouldn’t wear this exact thing, but if you told me this was ripped from Kardashian Kollection for Sears (seriously, they couldn’t get Kohl’s?), I would believe you. Maybe when Kanye is forced to step in and make Kanye for Kardashian Kollection for K-Mart, he can bite this design for himself.
But obviously, her crowning glory was the vagkin. It got her this far. Can it get her any further? Can it get her past this?
That outfit is what I imagine concussions look like. How could she DO this to that poor innocent coat?
Much like with Adrienne, people often wonder who the hell Rita Ora even is. Like Adrienne, she dated Rob Kardashian; unlike Adrienne, she got out quickly. Like Adrienne, Rita Ora is a singer; unlike Adrienne, Rita is benefiting from a massive, massive push from Unnamed Forces — actually, it’s Jay-Z; she’s on his record label — who keep her in the spotlight even though her first album’s planned U.S. release was canceled (although not before she shot a really bland cameo singing on 90210, which surely didn’t help). We hadn’t even featured her on GFY before August, but in our mammoth catch-up post full of hideous eyewear and ugly outfits, we could already tell she had Fug Madness power. It’s tough to pick a WORST from that collection, but I nominate this:
It’s… a dry-cleaning accident?
It’s… a college student’s laundry bag?
It’s… an abomination? As was the time she wore something off a Bridal Emporium clearance rack and then knocked her hip so far out of joint it looks like they airbrushed a stool out of the shot. world’s blandest peach satin AND she dragged a cat into her campaign. WHY CAN’T PEOPLE LEAVE CATS ALONE FOR A WHILE.
And mice:
Mickey is like, “Man, I have SO been there after a Stilton bender.”
So who’ll take it: The girl for whom Jay-Z should do better, or the girl who may not know better?
Archives: Rita Ora, Adrienne Bailon
(8) VANESSA HUDGENS vs. (9) KATIE HOLMES
Katie Holmes probably never anticipated that marrying Tom Cruise would cause a fashion problem for her. Because now that we know she’s richer than we can imagine and used to go shoe-shopping with Posh and whatnot, we perhaps unfairly expect her to be on another level. To do better. And it just never seems to happen. This blue thing looks like it cost $6, and not in a “WOW, that was only SIX BUCKS? WHERE?!?” kind of way. And this is super matronly:
She is the oldest 34-year old in history. And I’m sorry, but any ex-Mrs. Tom Cruise, except possibly Mimi Rogers because she got him at the height of his youth but not the height of his bank account, should be able to find something that fits better than this does.
Or a skirt that doesn’t look like Depression-era rags.
Or something that isn’t this:
Even Suri seems to feel betrayed by this precise jumpsuit-cardi-bootie combo. Katie is a long, lean drink of water who really loves a frumpy-cut pant.
Vanessa Hudgens, the outgoing Fug Madness champion, is on the record — pictorially, anyway — as loving an ugly-cut pant.
Or in this case, an ugly-cut brief, which looks like Fred Flintstone’s favorite skivvies. She also wore a new pair of the see-through lace ones she rode to last year’s victory, and almost everything she wore to Coachella — a music festival that is one long glorified paparazzi orgy, so there is no pretending these people don’t know they’ll be parading their clothes in front of photographers — was hideous in the extreme.
But lest we assume Vanessa’s candidacy this year is rooted solely in the appearance of vagrancy, we should look at some of what she wore when she tried to be fancy.
It’s… an ab ladder. A labder?
… the shoes could be worse? But the rest of it was last seen with a Thanksgiving turkey and novelty place cards sitting atop it. And this Globes gown is too old and potentially too much like Attack Of The 50-Foot Christmas Tree Tinsel.
Who should win: The girl who by all rights out to look like a million bucks, or the girl who looks like she’d insist on spending her million bucks in the very darkest parts of Anthropologie?
Archives: Katie Holmes, Vanessa Hudgens
(5) JENNIFER LOPEZ vs. (12) ELIZABETH BANKS
“HOLA LOVERS. And so we are here again, and Tyra Banks thinks she can beat me at Si Madness.
“Ay, lovers, it is so adorable that Tyra sent in this body-double to wear her silly clothes, and… eh? Que? It is some other Banks? Can’t people be named other things? Besides, lovers, Chase Banks does not know how to wear dramatic black bodysuit thingies the way that I can. And she might think she can wear sexy black dresses, but lovers, that is about as sexy as a Marc during a B-positive shortage.
“THIS how you do the black, lovers. Leg it up and LIVE.
Banks of America also thinks she can wear the sexy and the see-through:
“Ha ha, nice try, but let me WITHDRAW your self-confidence, amiga, HA HA HA HA:
“What is next for you, Wells Fargo? Do you think you can beat me at crazy?
“Lovers, I will not deny, this is muy dificil. I must shrug.
“Because her gown is very ugly. It is a pelvis tray. It is a fashion mustache. And lovers, yo will not deal with things that are silly. I am a woman who makes caftans have cleavage. I am a woman who wears TURBANS OF LOVE and gold lame dance pants! Am I supposed to be afraid of Agent Cody Banks and her Maxine Headroom hair and dresses that would give Marc the vampire twitches?
“Lovers. My backside frowns at you. Have faith that I can CRUSH Blood Bank. Porque Even when I am not trying to win, even when it is bad to win. CLEAR THIGHS FULL PARTS CAN’T LOSE. SOY LOPEZ.”
Archives: J.Lo, Elizabeth Banks
(4) JESSIE J vs. (13) SELENA GOMEZ
It was an interesting year for Jessie J, because she did try a lot of dresses that were more tastefully sexy. But she also busted out this hot pink leopard crotch-cradling catsuit, a cycling outfit that’s an ode to monochrome Twister…
… attempted formalwear that COULD have been pretty had it not so resolutely insisted on being part-leotard…
… and pajamas.
It didn’t stop there. We also got Attempted FormalwearShe kindly molted at the Queen’s Jubilee concert, and then decided to represent her country in the Closing Ceremonies wearing first a poorly concealed nude bra with some sequins that looked sneezed onto her body and then a one-legged bodysuit:
A questionable decision. I feel like, it’s no wonder she backed off of these — the Queen, and also probably the remaining members OF Queen, probably called her personally to suggest that she give it a rest lest everybody think Exhibitionist Fug is England’s chief export.
Too bad they didn’t get through to her before she wore the world’s most awful pants which will make you gasp when you click the link, or these strange non-pants.
She kind of looks like Vanessa Hudgens in this shot. Please nobody show the Hudge this photo in case she gets an idea.
I would suggest V’s Spring Breakers co-star Selena Gomez could help keep her attention away, but Selena — who divested herself of Justin Bieber in the nick of time — has her own problems.
Specifically, that she might be taking SHOPPING advice from her pal. That ratty peekaboo shirt is like a Hudgens-Cyrus hybrid.
Why does that crop top exist? And is it even denim, or just printed to LOOK like denim? If a tree falls in the forest, but no one is around to hear it, can we still arrange for it to fall on top of every version of this shirt that exists in the world? And maybe we can get it to destroy her hot pants as well.
Spring Breakers itself has been great for our Gomez archives. She’s worn a blue dress I thought was proportionally all wrong and which looked like a loofah had eaten her neck, an ornate gilded transparency, and a debatable bedspread.
And let’s not forget the body shaper that’s in the throes of an as-yet-undiscovered marine-life plague. Oh, and she also loves a questionable pantsuit:
Maybe she and Jessie J should go bowling.
Archives: Selena Gomez and Jessie J.
