^ Well, Cary Grant grew up in the slums of Bristol, England with an alcoholic father and his mother in an insane asylum, dropped out of school in the fifth grade and went on to become the biggest box office star in Hollywood and the on
and off screen standard of the world for the sophisticated gentleman - so....
Point taken. However, he did have to his advantage growing up in a era where all men were expected to dress up and dress well and where it was not uncommon for men to wear suits and hats and dressy clothes all day every day, whereas Leighton has come of age in an era where anything goes fashion wise, where there are few, if any rules..
While I do vastly prefer Blair's style to Leighton's style, I think Leighton's is pretty classy for what it is (urban hipster rocker?). While she has her misses, I don't think she purposely tries to come across as trashy or vulgar in how she dresses. And I like that she's such a free spirit. I suppose if I weren't a feminist, I might think otherwise, but I applaud her for not trying to fit into any mold--fan, Hollywood, or media.
(And, yes, even I find it killingly ironic that the fashion styles I try most to emulate in my personal life are those ladylike preppy Blair Waldorf, Princess Diana, Jackie O, Duchess of Windsor, Audrey Hepburn, Grace Kelly styles despite identifying as a feminist.

Boomer, I think it's safe to say I enjoy arguing with you.

(I'd love to hire you to be MY stylist though! If you were, I know I'd always look chic!

)