The offender: Alexis Bledel
The item(s) in question: Dress and shoes, worn during the Teen Choice Awards
My thoughts: First of all, I don’t care how many “Traveling Pants” she wears…to me, Alexis Bledel will always be the fast-talking, neurotic in an adorable way, straight-A student, Rory Gilmore. But back to the clothes. I’m sure this is a vintage dress, and I respect vintage most of the time. This time, however, it just looks like an old bridesmaid’s dress that someone gave to Goodwill because they never thought they (or anyone else, let’s be real here) would wear again.
The solution: Choose something that does not make these three thoughts immediately pop into one’s head: 1) Wow, that’s blue. 2) Um, that doesn’t fit. 3) Did she change outfits and forget to switch shoes?
thetightropeblog.com 
You forgot to mention the awkward stance, accompanied by the awkard smile-head-tilt thing she's got goin' on. But, all-in-all the outfit is pretty embarrasing.
i like the shoes with the dress, but i also hate the dress. it's like an 8 year old's easter dress or something. i don't think she's having fun with fashion, i really don't.