Fug Madness 2011, Elite Eight: Madonna Bracket

(2) MILEY CYRUS vs. (5) JESSICA SIMPSON

Interesting matchup here. I suspected Miley Cyrus might really make a run at the title, but Jessica Simpson’s success, I did not anticipate. Beating Katy Perry is no mean feat. As I said to Jessica yesterday, “Who knew good ol’ Jessica Simpson would have legs in ths thing?” And yet:

It’s as though Jessica were planning ahead for that wordplay. Much like I am concerned she was planning ahead for her run in Engaged To A Giant Lunkhead Madness, and also, Actual Madness Madness.

Miss Miley, however, wants you to know that she has legs as well.

Legs, and a crotch. I was THISCLOSE to censoring this, a la Taylor Momsen, until I realized that I think part of that circle in her skirt is INCREDIBLY strategically placed. But it still makes me want to cry. And I’m pretty sure that shirt has blitzed any chance she had at singing a romantic ballad at this summer’s royal wedding. … HA. Can you imagine? I would really, really love to be in the room when Wills and Kate decide to prank the Queen by telling them they want Miley to sing “The Climb” as Kate walks down the aisle — or better, have her perform “God Save The Queen.” I think perhaps Buckingham Palace would release a terse statement explaining that Ms. Middleton had been locked in the tower.

Also not singing at the royal wedding — or, sadly, much of anywhere:

Doesn’t matter how much Victoria Beckham you wear, girl. You are NOT royalty-adjacent. And your boobs are not remotely size-adjacent to that bodice.

Miley struggles with that as well:

Usually we have to beg people to hoist them up, but I just want her to let them relax. They’re BOOBS, not neck warmers.

This outfit is just… it should not have been allowed to happen.

Like, Michael Kors was RIGHT THERE. Could he not have told her it didn’t work? Could he not have said, “Honey, you need an empire waist and sleeves”? Could he not have tackled her backstage and exfoliated the orange off her skin? Was she thinking that looking like a football player would be very attractive to her ex-NFL player beau? HONEY.

And why did THIS happen? I’ve decided this was what Colonel Sanders’ childhood sweetheart wore, before she was tragically run over by a horse and buggy at a hayride. So he wore the tie the rest of his life as an homage, and also stayed far away from white layer cakes. The dude was complex.

These pants are not complex. They’re just awful. But then again, so are Miley’s.

Yikes, Miley. The bellbottoms toll for thee. I think my favorite part about these flares of tragedy is that they look like they’re made of paper. A lesson: If you’re going to wear something ugly like that, at least make sure it’s really high-quality ugly, or else our sad faces get more epic. I mean, come on, kid:

What IS that? The Forever 21 store at my mall just threw up a little in its own mouth.

So did the Macy’s, where a number of fine Jessica Simpson goods are sold. You know, I think one of the reasons her shoe line is successful is that she probably has the same attitude toward footwear as many of us do: Specifically, that it’s easy to care about them being comfortable and cute because they ALWAYS fit (by and large), even when the rest of your outfit looks like you were draped by an inebriated canary. Which, you know, sounds way more FUN than Cinderella’s earnest group of animal tailors, but also way less effective.

If you had asked me at the time, I’d have said, “Oh my God, Jessica Simpson is doing the Walk of Shame from John Goodman’s house.” Because that shirt clearly came from Ed’s Big & Tall.

As opposed to this, which looks like it’s from Fleetwood Rack, a Stevie Nicks-themed discount store run by Lindsey Buckingham’s older brother:

Either that, or Miley has discovered a truly special item of clothing known as the Wearable Hammock. Anytime you’re running a little low, just find two trees and string yourself up for the catnap of your life. In some ways, I can’t believe Jessica Simpson didn’t wear this. Perhaps her posse of Friends Who Enable Jessica To Really Horrendous Decisions did not complete all its tasks this year.

They were, apparently, too busy tweeting Miley that dressing like Step Up 4 The Team: Soccer Dance Fight 4D was a brilliant idea. Then again, maybe Team Simpson Sabotage felt like it had already done enough. Did it?