A: First swear to me that you won't get down on yourself. You can look terrific at any weight—but you have to stay in the present. Shop for the size you are now, not some future, skinnier you (you can always get stuff tailored later).
Start with a full skirt. It skims the danger zone of the hips without clinging, and I love the flirtatious way it moves, making you feel pretty, sexy, and feminine. Avoid loose, schlumpy-looking tops. You don't want skintight, but make them fitted enough to balance the big skirt.
As for pants, I've got to be honest—ultraskinnies don't work for most bodies. Leave them to 18-year-old, size 4, Lindsay Lohan types and get a classic, straight-leg pair that sits right at the waist. No low-rise, no pleats.
No strange colors, either. Black and other neutrals are always slimming, not easily dated, and (lucky for you) in major abundance this season.