Blake Lively
She has by this point slid seamlessly into the Serena Van Der Woodsen aesthetic -- which was always a little beachy-tousled. This walks the line between "I'm in a movie that's still sort of for kids and young adults" and "I'm in a TV show that pretends to be for young adults but is actually for adult-adults and everyone's cleavage is a big part of that."
Wait, do we think her dress was... caught by the wind? It kind of looks like someone off-camera is fluffing it.
America Ferrera
America was of course on Ugly Betty, so she here is deploying more fashion than she was ever permitted on that show. The dress is cute but if she wriggled around in front of you the swirls on it might cause hypnosis.
Alexis Bledel
This definitely has STYLIST written all over it, from the bag to the shoes. This is not a bad thing, by the way. Stylists exist for a reason and I would argue are maybe MORE essential for the younger actors starting out than for the established ones. So this has a sophistication that we hadn't seen much of from the erstwhile Rory, although it's a wee allergic to flashbulbs.
Amber Tamblyn
This is not my favorite thing but it's ALSO of-the-moment and has a disco-grooviness to it on her. Amber was never one to care that much about the styling, I don't think, so something that felt trendy but also simple fits her vibe.
Jenna Boyd
I mean, she was 15. WHATEVER is happening here was probably very hard to resist for a 15-year old in 2008, even if it did come with rib pockets.
Becki Newton
This has a whiff of "I want to look like I went digging in the Vogue closet," which is also apt for an Ugly Betty costar. (I miss Becki Newton; she was funny.) The pants under dress are perplexing, naturally. As ever. Always.
Leighton Meester
Blair Waldorf looks good. She had to be pretty OTT on Gossip Girl, so keeping it simple makes sense.
Ana Ortiz
She looks cute, too -- and is ALSO an actress who is heavily styled on-camera so probably kept it streamlined on her own.
Jurnee Smollett
She may not agree with me, but I am into that blouse.
Tamara Feldman
Tamara "Poppy Lifton on GG" Feldman here has on a super breezy summery dress, and I quite like it, and then we get to the boots and I'm confused by what the weather was where her feet are.
Chrishell Stause
She had broken it off with Matthew Morrison at this point -- I think a year earlier? He was apparently not a great fiance -- and while she rebounded with an adorable dress, she also dove too fast into a pot of highlighting makeup.
Nat Wolff
LOOK AT TEENY NAT WOLFF. He had just gotten his break in "The Naked Brothers Band" on Nickelodeon, and you would later seem (perhaps) in The Fault In Our Stars or Paper Towns or Admission. He's so wee. Apparently, humans start out young and then get older?!?!?! Who knew.
Mark Indelicato
He was adorable on Ugly Betty, and is adorable in this outfit.
Ed Westwick
Meanwhile, Chuck Bass cannot be bothered to button his shirt fully on either end.
Chace Crawford
And that shirt appears to have been balled up in the corner of his room, and I think he wore those shoes hiking.
Jesse Williams
He looks terrified, and I love his stripes.
Michael Rady
Oh, Kostas, is that your grandfather's suit?
Graham Bunn
I had to look this dude up, and yes, he was on The Bachelorette and then turned into some kind of mild TV personality. And yes, for sure, those shirttails look ridiculous.
Matthew Settle
"Yep, totally saw the first one, it's about... pants... that travel. NAILED IT, gonna be great."