I went in February last year and I wore jeans almost everyday. I'll be going in February too, so from past experience, I plan taking 3 jeans, 2 shorts, 2 sweaters, a bunch of short sleeves shirts and probably just 1 pair of capri pants. It didn't rain until our last day there, but perhaps take a small 'brella just in case. Also need the fancy business attire outfit for the Floridian and Emerils.