Fug Madness Round One Continues With One Tony Winner, Some Grammy Winners, and Also Some Other People

First! Did you miss our editable bracket? This link will open it! Next: The photos we show aren’t the ONLY ones in consideration; just a representative sample of everything worn from after the Oscars in 2019, through Feb. 10, 2020. Polls close after roughly 24 hours. Vote on any device, as often as you want to or can. 

Jump to the polls:

(2) Ben Platt v. (15) Kendall Jenner · (7) Halsey v. (10) Florence Pugh  · (3) Christina Aguilera v. (14) Charlize Theron · (6) Carrie Underwood v. (11) Kacey Musgraves

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(2) Ben Platt v. (15) Kendall Jenner

Obviously, I think this is a match-up we all saw coming from a mile away; two houses, alike in dignity, in fair Fug Madness where we lay our scene. Tony winner and Netflix star Ben Platt makes a SPLASH in his first Fug Madness. Earlier this year, I said he “often looks like the sassy old man you ran into next to the Jell-o salad at the buffet at your parents’ golf club,” and I stand by that. Exhibit A:

Also falling into that category is this, and also this, although those we at least downgraded his age to “golf pro.” And, of course, this:

We also said he often looks “about 15 percent too styled,” which I also stand by:

Who could forget the time he, as Heather said, tried to sell us a monorail:

I feel like we’re also dealing with a situation where perhaps he is a bit too enamoured of the fashion stylings of one Cosmo Kramer:

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Part of the issue might be his real love for Steve Urkel-level trousers:

Satin is a risky move for a man or a woman:

Ditto wide-legged leather trousers:

I don’t even know what to say about this combo:

I mean…I do salute a man for making an effort???? Sincerely!

Speaking of making an effort, Kendall was much more low key this year than she was last. Her Met Gala look was stunning, as was her post-party effort, but she must have mostly kept her head down and worked.  (With the except of the Emmys, where she took a BIG RISK, sartorially speaking, and a brief, surprising break to go blonde. And of course when she showed up in something inflatable.)

I am confused by these sunglasses:

And ALL of these accessories:

I am DEEPLY concerned by the return of the Visible Fashion Thong:

And this is SO short that I have to think she’s actually wearing shorts underneath it. It would be too emotionally terrifying otherwise:

In case you were wondering the the early aughts might be making a comeback, Kendall is here to prove that this is absolutely the case:

Did you think this game would include Possibly Misguided Leather Trousers v. Possibly Misguided Leather Trousers? Because I did not. AND YET:

Get your vote on:

(7) Halsey v. (10) Florence Pugh

Halsey went deep in last year’s tournament, and was the runner-up in 2018, losing ultimately to the unstoppable force that was Bella Thorne that year. Can she go far this year? We’re about to find out…but first she has to get through Florence Pugh, whose rookie season was super strong — both in terms of her actual career, and here.

When I covered this the first time, I literally said, “Get ready to see this in her 2020 Fug Madness run.” And HERE IT IS:

This is likewise a slam-dunk for these purposes (although the Pride flag part in her hair is rad):

And THIS is TERRIFYING. Halsey, what?!!?!!!!!!

What a STRONG start. We’ve also got her facially amazing but somewhat off-topic Met Gala look, this weird leather scenario, this wacky and dangerously boob-y gown at the Billboard Music Awards, and this uncomfortable garbage bag situation.

And, of course, this:

I love that Florence Pugh burst onto the scene with such sartorial bravery. I deeply enjoy everything she tries, even when it isn’t 100% right. Look at this MASSIVE SLEEVE:

Remember that time she dressed as a Valentine?

(You should know that dress also has big holes in the side.) Florence is driving HARD to be cast in an 80s movie and honestly I wish someone would take her up on it. She’d be GREAT in an big, blowsy, dramatic 80s period piece! Imagine her wearing this in its climatic emotional sequence:

I would watch her cry beautifully in the rain in that! (She’d also wear this in that movie.) (And this!)

Not everything was so bombastic. This was underwhelming, by her standards, and this maybe NEEDED some bombast. This also needs a little extra zhushing, perhaps? (This needed NO MORE zhushing.) This is just mildly wacky.

This skirt was confused about skirts:

And this just felt like she was tired — and who can blame her? She had a big year.

To the polls!

(3) Christina Aguilera v. (14) Charlize Theron

Xtina didn’t come out a LOT this eligibility period, but she made it count when she did. She could have been included on the strength of this alone:

This is a LOOK and possibly also a sentient loofah. I BLESS Xtina for going for the gusto.

Speaking of gusto:

You should know that the train on that gown continues for QUITE a ways. And while we are discussing the lost art of understatement, behold:

She did indeed wear that in Paris.

Also on theme:

That was at the premiere of some Addam’s Family something or other. Never let it be said that Xtina phones it in. Speaking of NOT PHONED IN:

I enjoyed this at the time, but this is not…technically not something an alien queen might wear when she decided to swoop down to earth.

In a more terrestrial turn of events, Xtina also had a lengthy period of wearing boots instead of pants. Like so:

That’s just a blazer and boots. So is this:

And this is just boots and a top:

Has Christina forgotten what BOTTOMS are? It seems possible.

And finally, I leave thee with THIS. It DOES, to reassure you on the above, have trousers:

Does that technically count as an entry into the Sexy Tootsie sweepstakes? Please let me know.

To Charlize! Who spend a lot of this eligibility period looking underwhelmed in whatever Dior (or McQueen) made her wear. This is clearly a violation:

As I said at the time: CHARLIZE, IT’S SHEER.

Charlize, it’s ALSO sheer:

Charlize, it’s a MUDDLE:

Charlize, it’s NOT FINISHED ON ONE WHOLE SIDE:

Charlize, it’s A PILLOW CASE:

Charlize, it’s FALLING OFF YOU:

Fug Nation, it’s time to VOTE:

(6) Kacey Musgraves vs. (11) Carrie Underwood

Two country superstars, head to head! Carrie, so often a strong force in this challenge, had a rather low key year — in part because she had a baby in later January 2019. This look — three months later — says, “NO ONE TOLD ME that people would be taking my pics at this event!!!”

SOMEONE got all-caps email about this.

And I’m gonna send an all-caps email about THIS:

It’s going to say, “CARRIE UNDERWOOD! How could you wear that next to Reba McEntire!” Which, in fairness, looks like exactly what Carrie herself is thinking.

I don’t know what she was thinking HERE:

Must a formal gown have a LOINCLOTH? I do not believe that to be an actual requirement.

This isn’t terrible — she actually looks great in it as a human (which she usually does, to be honest, as she is a good-looking person) — but the longer you look at it, the more it’s clearly two dresses from two different seasons melded together:

But it’s paradise in a gown compared to:

AHHHHHHHHH.

But please segue with me to the wardrobe of one Ms Kacey Musgrave. Can Carrie take down a woman who wore a Chanel snowsuit to a dinner?

What about someone who so bravely risked green-screen shenanigans, or two matching jackets at once, or what might be a salute to Cher’s wax figure? Or…this:

I actually think I might like to see that on Carrie? It has the potential for greatness.

This next one is just perplexing. It’s not the dress, but look at her ankles. They just have…tulle wrapped around them?

This is wonky, proportionally-speaking:

It sort of looks like it’s meant for a person who is a foot shorter? How does that work?

This feels — like Xtina before her! — like she’s wearing a Scrunchie with aspirations for more:

But, as with Carrie, I need to end with the look that caused me to shriek aloud, a little bit.

Time to vote!