Ashlee Simpson
Where do we even begin with this outfit? Seriously, how did this look ever see the light of day? From what we can see here, Ashlee Simpson is wearing a long tutu skirt, tall baseball (or bowling?!) shoes, a sheer camisole layered over a t-shirt, and a low-hanging belt.
Why didn’t anyone suggest removing at least one of these fashion faux pas? Like the others on this list, Ashlee Simpson has grown up since then, or at the very least, she’s enlisted the services of a stylist!
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