Jessica Simpson This dress bums me out. It's not only boring, but a fugly execution of a tired idea. Jessica needs to beg Law Roach for a solid. She could be a camp sensation and I think that would be SO much more fun AND maybe an injection

Naomi Osaka Naomi is really carrying on Serena's legacy of wild outfits. (In one of her interviews, she remembered a particular defeat as bothering her because she had been in one of her favorite ensembles.) The purple poof is the one she wore for almost every round after

Drew Barrymore Drew presented the Video Vanguard award to Michael Jackson. Why that necessitated a platinum wig, we may never know. This was just a few months after she flashed David Letterman atop his desk. She was obviously... trying things. Madonna This is so SENSIBLE for Madonna. And indeed, this

Gwen Stefani This is perfect on Gwen. I love this era of Gwen. I wish the current Gwen would dig this up and wear it again. Lindsay Lohan I truly, truly had to double check my eyesight that this was Lindsay, and not her mother Dina. Jessica Simpson and Nick

Busy Philipps and Michelle Williams (in Dima Ayad) Busy's dress is fantastic and I am having a better day for having seen it. Michelle looks like someone tailored it by binding her with scrapbooking tape. Lin-Manuel Miranda Sure! He maybe did throw away his shot a little,

Jason Momoa I love his pink suits. I love even more that he matched his Birkenstocks and his toenails to it. Momoa has always been very proud of pouring his giant manliness into colors traditionally associated with femininity, and he does it well. At first I thought he was in