Cher Bracket, Round One: Featuring Leonardo DiCaprio Branded Pants. For Real.

We once noted of Keke that she is one of those celebs who inspires great joy in us, because whenever she arrives at an event we know she will either look truly fab or completely bonkers (or somehow both), and either of those outcomes will bring joy to us all. She is never EVER boring, and I always give points for that. Keke does not shy away from the occasional buttcheek moment, as the fashionistas would call it. She enjoys a fur accessory. She digs a bra top, like truly truly loves a bra top, like, CANNOT RESIST a bra top. CANNOT AND WILL NOT:

She wears a latex dress better than reigning champ Kim Kardashian. She loves Leonardo DiCaprio, like, a lot:

Her Instagram is likewise a TREASURE TROVE and I recommend following her:

What did I tell you about the bra top? She’s obsessed. Oh, Keke. I enjoy you. (She was also, FWIW, a total hoot on Watch What Happens Live a couple of months ago, and I think she’d be fun to be stuck in an elevator with. I can’t help it. I enjoy her.)

As for Aja, I just discovered that we own the same tee-shirt:

I have not yet purchased this, however:

(It sort of makes me laugh that she’s wearing this to something sponsored by Colgate. It IS kind of like Fancy Toothpaste In Dress Form.)

This dress feels like it’s related to the other, just simply in black in case she wants to sport it after Labor Day:

Luckily, you’re allowed to wear a tablecloth as a skirt all year round:

What would Annalise say?!

For further edification, you can find Keke’s archives here; Aja’s are here.

 Loading ...

8. Carrie Underwood vs. 9. Dascha Polanco

I regret to inform you that Carrie had a very bumpy ride this year; I may have squawked the word “YIKES” more than once when pulling this head-to-head together. I do not regret to inform you that this is going to be a super close match-up, I think. Which is always fun.

What prompted my first scream? BEHOLD:

Heather pointed out at some point last year that part of Carrie’s issue is that she often veers to the cheesy. At some point, she may have veered to the land of the bike shorts? And she’s renting a very large AirBnB in Sheerlandia.

She also has a cute pied a terre in Wow That’s Short-ville:

And she may be slowly turning into a bird:

Over to Dascha, who is a delight to me; I also think she is great on OITNB. Having said that: I wish she had decided against wearing this tuxedo jumpsuit to the SAGs. I’m also not sure that I think this fur is the best idea, although I appreciate THE DRAMA inherent. And this is also dramatic in the sense that it feels claustrophobic.

As for this? This just hurts my feelings:

Here, there is something to be for wearing a red lip both on one’s face and on one’s pants:

Please don’t contribute to the revitalization of Dress Over Pants, Dascha. Don’t we all have enough problems?

Before you vote, if you need more intel, don’t hesitate to examine Carrie’s archives. You can find Dascha’s here.

 Loading ...

5. Diane Kruger vs 12. Solange

Two fashionista enter! One fashionista leaves!

Let us begin with Diane, Pacey-less and worse off sartorially than in past years. I’m sure you remember the disaster that was her Oscars party dress. But many of these also-terrible looks may have fled your memory banks. This, for example, is tragically bland. This tortures her cleav. This almost gave me a heart attack. This is what it looks like if Diane Kruger chooses to wear the inside of a handbag. This looks like Batman started an evening-wear line. This feels terribly over-styled:

This is just objectively heinous:

This is sort of sad and underwhelming:

And this is like Droopy Shakespearean Lass:

Solange loves a dramatic pant. AND a dramatic suit:

She wore a LOT of lame this year, which always brings me joy:

And if you think that was her only foray into Intriguing Pleats, please allow me to refresh your memory WRT the Met Gala:

And please never forgot that she once wore packing material:

(Beyonce looks really great in that photo, also.)

For your research purposes: Diane’s archives, and Solange’s archives.

 Loading ...

4. Ashley Graham vs. 13 Kristen Wiig

It won’t surprise you to know that Ashley Graham — who was GREAT on the judging panel of this past season of ANTM, FYI — spent a lot of time in sheers this past year, which meant that we saw a lot of her granny panties. And when she wasn’t in the sheers, she got somewhat squeezy. This is ALSO very squeezy. This is just half-assed. But her high seed was well and truly earned by one look. One unforgettable life choice:

OH ASHLEY WHY.

Also so much why:

Speaking of why, I know the answer for this one. It was literally a lingerie event. STILL:

I think Ashley would also wear this, frankly:

How did that not happen? Also, while this next look is NOT good, it IS a kind of amazing example of how a different haircut and color can totally transform a person:

And, in another noteworthy look, I sort of loved this look, but also recognize that she looks like she’s wearing the background of the Vans store in 1983:

That dress really only makes sense if she wears it holding an inflatable flamingo and stands in front of a wall of glass blocks.

La Wiig actually went ALL IN on patterns this past year, which I actually do appreciate:

If you need to look at Ashley Graham’s archives, they are here! La Wiig’s live here.

 Loading ...