Ashley Tisdale
Ashley Tisdale unquestionably had some of the most audacious outfits of the 2000s. In all fairness, she was a teenager navigating newfound fame, and her expectations were high for appearing chic at events. Did anyone provide her with a stylist? Did anyone even have stylists in the 2000s?
In this eccentric ensemble, the actress wears a long, ruffled slip dress layered over a t-shirt and straight-leg jeans. She accessorized with a knitted beanie and a sequined tote bag. Fortunately, she has moved past this look since then.
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