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The new Halloween, by virtue of its name, is mostly focused on the holiday that sees kids dress up in costumes looking for candy. However, one of the characters, Judy Greer's Karen, seems to be celebrating a different holiday, as we see her wearing a traditional Christmas sweater throughout much of the movie. While never specifically referenced in the film, it seems that Karen's upbringing as the daughter of Laurie Strode has led her to hate Halloween, and as such she starts celebrating Christmas a little early. According to Judy Greer...
There's that little sign of rebellion. On Halloween, she wears a Christmas sweater so that she doesn't celebrate.
The new Halloween takes place 40 years after the original film and sees that Jamie Lee Curtis' Laurie Strode has never truly gotten over the events of the original film. She has trained herself to fight in case Michael Myers ever comes back and she has also trained her daughter Karen to do the same, something Karen never truly accepted. One assumes that the anniversary of the attack on Laurie was never an easy time in the Strode household. As Karen eventually rebelled against her mother and has become somewhat estranged, it makes sense that Karen just doesn't enjoy Halloween the way most of us do.
Judy Greer tells EW that the idea to have Karen skip Halloween entirely came from director David Gordon Green, but she embraced the idea whole-heartedly. While the movie never comes out and tells us why Karen is wearing a Christmas sweater, Judy Greer had a complete understanding of what's going on in Karen's head.
Like, as soon as the tiny little bite-sized candies come out in the drugstores for trick-or-treaters, she pulls out her Christmas sweater and is like, 'Nope, nope, I celebrate Christmas, I'm just skipping right to Christmas.'
It's a great little element that adds a bit of depth to the story. If you notice that Karen is wearing a Christmas sweater you might even be able to piece together in your own head why she might do that. Her rebellion against her mother and her feeling that there's nothing to fear is made clear, even if her specific hatred of Halloween is not.
It seems that the new Halloween is simply littered with little ideas like this one. Recently, Jamie Lee Curtis spoke about how she decided that, in one early scene, Laurie Strode would be drinking strawberry milk because it's the same thing she drank in the original Halloween, and Laurie Strode is still very much in the same mental apace as yer 17-year-old self. Again, the moment is never explained and attention isn't really brought to it, just like the Christmas sweater, but it all makes sense if you think about it.