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Meghan Markle looked timeless and elegant in a black fit-and-flare dress in 2018

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[7] On Friday 17 March 1995, comedian Dawn French wore a copy of the dress (over a white vest) in a sketch for the Comic Relief telethon where she kissed Hugh Grant

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Both low and high-rise platform sneakers will look good, though high rise are the best way to go if you don't want socks peeking out