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Holly and Jade make me think of somewhat similar people, but Holly seems a little older and Jade seems a little prettier. Both make me think of someone with dark hair. Holly makes me think of someone with glasses. Jade makes me think "green" more than Holly makes me think "red".
I don't think Holly is necessarily associated with Christmas or winter.
I don't think either of them are dated, but I'd be a little surprised to see Holly on a young kid (and I wouldn't be surprised to see a young Jade at all).
I prefer Jade, but I usually use it as a middle name in combos.