Crimson Cutie
While on the Gossip set, this Upper East Side cutie struts the NYC sidewalk in crimson-wicker sandals, a denim shirt-dress, and a skinny red belt to match her lip.
Busty Blake
In typical fashion, the G. Girl shows off her assets at Comic-Con ... but is this to diverge our attention from what's below her waist? Hey Blake, MC Hammer called. He wants his pants back.
California Girl
Blake is summery cuteness in Chanel at the brand's fashion show in Paris.
Badass Babe
The dark angel to Blake's nice girl, Leighton rocks tough leather in the summer.
Sweet Chic
Blake's not showing off too much leg or chest in this darling white dress in Paris.
Underwear as Outerwear
Taylor struts the streets of NYC in all her lingerie glory.
Pretty in Pale Pink
Love this adorable look on L.M. She can be so pretty when she's not trying too hard to be edgy.
Teenage Wasteland
Careful, Taylor, one wrong move and you're gonna flash your Little J to the world!
Blue Belle
At the Costume Institute Gala, Blake wears a blue mini that's not too far off from what she wore the year before.
Acid Test
It's a mix of cool and cute. Leighton def got it right this time!
Night Moves
The 16-year-old Taylor wears her fave dress: a nightgown.
Harley Honey
Blake Lively ditches the Upper East Side for biker chic at the Ray-Ban Remasters in 2008.
15 Going on 30
Taylor Momsen is happy and her girls are perky in this Marchesa gown.
Be Still My Heart
Blake Lively looks pretty in pink outside the Late Night studios.
Blake Lively at CFDAs
The actress sports this electrifying cashmere Michael Kors dress at the annual Fashion Awards.
Put This Together
Leighton Meester's Emilio de la Morena outfit at an event for 500 Days of Summer is puzzling. Literally.
The Queen at Chloé Boutique Opening
We needed a picture of Leighton Meester in orange to complete our colors-of-the-rainbow gallery. (Otherwise this one would not have made the cut.)
Circus Act
Leighton Meester is not really a clown. But this Louis Vuitton garb (what else can we call it?) does not do the poor thing any justice.
Hot, Hot, Hot!
Jessica Szohr is our choice in this Alice + Olivia layered tiered dress at the 2008 Teen Choice Awards.
B Blooms
Leighton resembles a daffodil at the Paley TV Festival—this wilting flower needs some Miracle-Gro.
Night at the Opera
Leighton attends La Fille Du Regiment in a yellow strapless Yves Saint Laurent cocktail dress. The good news? The cut is flattering. The bad news? Don't get us started on her hair and whatever that is around her waist.
Give the Dance Team Back Their Uniform!
Meester misses the mark in this reptilian outfit at the February 2009 Erin Wasson+RVCA show.
Emerald City Meets Window Drapes
Awww, Leighton...It's called the "Teen Choice Awards," not the "Grandma's Choice Awards."
You Know You Have a Slammin' Bod When...
...a painted-on space suit makes you look like a million bucks. Blake rocks this frock at the Entertainment Weekly-Vavoom upfront party in May 2008.