Family Holiday Party
A floral black and white will be classy and elegant for dining with the relatives. Make sure the fit is tailored, but not too tight. Also, pick something that buttons at the top. You can adjust it accordingly depending on whether or not you want to impress your family, or prompt whispers. Dull family? Then make up for it with some candy apple red heels.
New Year's Party
I'll admit that my initial reaction to the above dress was a negative, but for New Year's it just might be acceptable. If you're going to a fun dancey kind of party, go metallic. One-strap numbers are always fun if you've got the body, but for the modest ones, go scoop neck with quarter-length sleeve, tight fit. As far as shoes go, look to the nude shoes that are so in this season. However, some pinky flats might be a nice option to sweeten things up.
Christmas Eve Dinner
Sweater dresses are known to show off some of your less desirable rolls of pudge that are otherwise well-concealed, but as long as you've got a nice slip, they're surprisingly easy to pull off. This dress in particular is cozy, and would look great with white tights and some patent black flats. I would wear a bright strawberry pendant to really funk things up, but that's up to you.
Last Day Before Break
To kick off the holidays, try this sweet milk maid dress with a black cardigan. Go for things that look very Swiss Miss European. Add some black textured tights, and you're all ready to celebrate.