Damon is dressed here as Henry VIII. He's making the look work for him, isn't he?
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It's Halloween for Damon and Elena. They are dressed here as Anne Boleyn and Henry VIII.
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The Vampire Diaries Season 5 Episode 5 Quotes

Don't piss off the diabolical ones.

Katherine

The more I have to think about, the less time I have to miss Bonnie.

Elena