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5. Meghan Markle, 2017
How gorgeous is this engagement photo? Meghan donned a stunning Ralph & Russo gown for her and Prince Harry's engaement pictures, which were released by Kensington Palace. The floor-length black tulle gown was straight from the autumn/winter '16 collection and featured a silk organza skirt and a lace bodice with intricate gold feather threadwork. It's estimated that the dress cost about $75,000.

Some also criticized the dress for being too sheer for an important occasion like an engagement shoot. 
Risqué or not, we think the duchess looked gorgeous in the frock.