Hilary Duff
As a Disney Channel star, Hilary Duff was no exception to the questionable fashion trends of her peers. Here, we see her wearing a flower rosette with chains hanging from a pair of low-rise combat pants. Seriously, will we ever get over this fashion blunder? This outfit includes a tiny 2000s bag (now back in style) and a striped tank top.
Reflecting on that era, it's safe to say that Hilary has become a much more polished dresser. She sports cute round sunglasses and an oversized trench coat in the photo on the right.
