Pretty Woman: Leather Boots

Worn By: Julia Roberts
Year: 1990
Value: $15,000*

There are so many memorable parts about 1990’s Pretty Woman that it’s impossible to list them all. However, Julia Roberts’ character Vivian undergoes one heck of a transformation. When Richard Gere’s high-flying businessman meets Viv, she’s wearing knee-high leather boots.

Roberts wears the boots on the movie poster too, which makes them doubly iconic. In 2020, the boots went under the hammer and were sold for a very cool $15,000. Vivian would have been ecstatic with that amount of money in her purse, but would she have parted with her favorite kicks?

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