To make it easier, I generally try to pick a "theme" and stick with it. I always plan specific outfits for specific days (based on the weather, yeah I'm a neurotic weather freak). Sticking with one color scheme gives me flexibility if I should happen to change my mind (imagine that).
For Hawaii, it was all things bright and breezy, bold colors and sheer fabrics (and, of course, a bikini for every day of the week) And as for New York, it's looking like a lot of jewel tones and earthy hues in rich, cozy textures.
[Rather than packing a lighter jacket and a heavier one, I plan on layering the vest under this utility jacket on particularly chilly evenings. Layers: the packing girl's best friend.]
[Strike that. The weather forecast: the neurotic packing girl's best friend]
What are your travel-savvy packing tips, my jet setters? I'd love to know. :)