A Lively Mishap
At the Miss Sixty fashion show in fall 2008, S makes the mistake of wearing this godawful pantsuit.
Pout Some More, Taylor
Judging from her expression, she'd rather be anywhere than the red carpet. Regardless, Miss Momsen has chosen a beautiful Marchesa gown for amfAR's Fashion Week gala.
Getting Sassy
Hello, gorgeous. We're not used to seeing Blake Lively (or Serena, for that matter) dolled up like a supermodel, but she looks stunning in Versace at the Model as Muse Costume Institute Gala at the Metropolitan Museum of Art.
Gossip About This
How jealous are you of those legs? Blake rocks the Adam shorts jumper with nude Christian Louboutin peep-toe pumps at the CW upfronts in May 2009.
Dressed in a Collage
Leighton shows up to the 2008 CW upfronts in a sack apparently designed by 5-year-olds.
Cute to the Max!
Blake is positively royal in this purple Tadashi Shoji mini. She also looks young! What a year in the spotlight can do...
Trip Down Memory Lane
Michelle Trachtenberg, did you miss the memo? Lisa Frank products do not belong on your body. (Although we might have given you a pass on this one if you were carrying a Trapper Keeper.)
Lady Leighton
This Nina Ricci mini is a winner on Queen B. What a beaut. We're speechless.
Style Clash
Reebok spokesperson Leighton show offs the brand's new kicks...which is unfortunate, because sneakers look a little frumpadelic with that otherwise adorable 3.1 Phillip Lim dress.
Blair Waldorf Would Be Proud
Leighton stuns in this classy Jay Godfrey dress at Reebok's Freestyle World Tour Collection event in February 2008.
Leighton Plays Cleopatra
Good thing the Upper East Sider has such great extremities—otherwise, this shapeless tunic would be incredibly unflattering.
Zebra Skin
Two things: (1) This jumpsuit is striped. (2) Leighton is on a date to a bowling alley. Enough said.
We Likey
Blake's decision to sport a Smythe jacket, Tory Burch jewelry and Chanel shoes to the Gossip Girl event at the 2008 Paley Television Festival earns an A+ from us.
Arrrgh, Matey!
Apparently Blake turns into a pirate when she drinks VitaminWater. Sound off on this shipwreck below.
Child's Play
Blake Lively looks like a little girl in this Chloé dress and tights at the Guggenheim Young Collectors Council Artist's ball in December 2007.
Blake Goes Back in the Day
We're not sure who picked out this outfit, but IOHO, velvet skirts were only cool for middle-school holiday concerts in the '90s.
Anything but Serene
Blake misses the boat at the Australia premiere.
Gala at Tiffany's
Blake looks like a goddess in this Alberta Ferretti gown last October. She even has matching bronze nails.
Blake in Ralph Lauren Black Label
During New York Fashion Week last February, the actress sports a fitted gray cashmere dress and a cognac-brown leather jacket. And might we add...the hair! We love her hair!
Taylor Momsen at the Transformers 2 Premiere
The youngest Gossip Girl transforms into someone far older than 15 in this Dolce & Gabbana frock.
Szohr Is Smiley
It's refreshing to see someone actually enjoying themselves on the carpet. Say cheese, Jess!
Leighton Tries a Pantsuit
Queen B pairs some shorts with a Jil Sander blazer at the 2009 CW upfronts.
A Creation by Edward Scissorhands
We're sorry, Leighton, dear—it's probably the camera angle, but you look like a bobblehead in this picture from the MTV Movie Awards.
Twinkle in the Eye
Adorable. We can't help but smile when we look at this pic of Leighton at the Sisterhood of the Traveling Pants 2 premiere.