At the Miss Sixty fashion show in fall 2008, S makes the mistake of wearing this godawful pantsuit.
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.
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.
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.
Leighton shows up to the 2008 CW upfronts in a sack apparently designed by 5-year-olds.
Blake is positively royal in this purple Tadashi Shoji mini. She also looks young! What a year in the spotlight can do...
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.)
This Nina Ricci mini is a winner on Queen B. What a beaut. We're speechless.
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.
Leighton stuns in this classy Jay Godfrey dress at Reebok's Freestyle World Tour Collection event in February 2008.
Good thing the Upper East Sider has such great extremities—otherwise, this shapeless tunic would be incredibly unflattering.
Two things: (1) This jumpsuit is striped. (2) Leighton is on a date to a bowling alley. Enough said.
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.
Apparently Blake turns into a pirate when she drinks VitaminWater. Sound off on this shipwreck below.
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.
We're not sure who picked out this outfit, but IOHO, velvet skirts were only cool for middle-school holiday concerts in the '90s.
Blake misses the boat at the Australia premiere.
Blake looks like a goddess in this Alberta Ferretti gown last October. She even has matching bronze nails.
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!
The youngest Gossip Girl transforms into someone far older than 15 in this Dolce & Gabbana frock.
It's refreshing to see someone actually enjoying themselves on the carpet. Say cheese, Jess!
Queen B pairs some shorts with a Jil Sander blazer at the 2009 CW upfronts.
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.
Adorable. We can't help but smile when we look at this pic of Leighton at the Sisterhood of the Traveling Pants 2 premiere.