I second what Ree said, watch "What Not to Wear"!
The hosts are so funny, and they do give a lot of good information out.
Since it's $1,000, I would invest it in some "basic" pieces that you can't go wrong with - meaning, simple pieces that you could easily mix and match with other pieces and layer with to create interesting outfits. Some include:
- A fitted jacket;
- Dark wash jeans;
- Good pairs of heels;
- A great night-out dress;
- Shirts that fit; long sleeve or short sleeve, in a solid color or lightly patterened
Once you have the basics down, you could buy different accessories to amp up the outfit as well. It might sound confusing, but after you watch WNTW and Google up some fashion things, it'll make sense. Hope this helps!