I get what you're trying to do here, Whitney Port, with the centre part, loose waves and backcombing.
I swear my mom had this hairdo once, and I don't mean that as a compliment. Actually, it looked better on my mom, I think.
Anyway, the reason why this isn't working for me is because it's just TOO retro.
Backcombing in general is risky. If you're going to do it, the best way is with a style in the vein of Kate Moss' shorter, curlier, bouffant, which looks way more modern than this all-one-length, "curtains" sort of effect. (Also note: when I showed you stylist Kristjan Hayden's version of backcombing, it worked because the waves in the hair started higher up on the hair shaft.)
I'm also not loving the heavy, obvious liner on the upper lash line. A smoky eye would have looked better with this hair. The combo of retro hair plus retro makeup is just overkill.