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Gillian Zinser attended the “Night of Firsts” by The Hollywood Foreign Press Association (HFPA) and InStyle at Cecconi’s restaurant in West Hollywood yesterday, while Demi Lovato made an appearance at the Z100′s 2011 Jingle Ball in New York earlier today. The two ladies dressed in completely different attires, but both donned a black hat. Who do you think wore it better?

The 90210 star wore a floor-length, long-sleeved, semi see-through black dress, which she paired with brown boots and a black hat. Her minimal makeup looked great, but we’re a bit confused on what Gillian Zinser is trying to pull off with the entire outfit.

Demi Lovato, on the other hand, has been wearing different hats on various red carpet events, so she’s pretty used to matching them to her current outfit. When she stepped out for the Jingle Ball, Demi wore a black dress, black tights, and covered up in a dark denim jacket. She wore the black hat on top of her newly self-dyed hair, which gave an amazing contrast to her red hair color.

For this round, we think Demi won the black hat face-off. What do you think?

Photos by: FayesVision/Ivan Nikolov/WENN.com