You sound a lot like me Rachel. I'm a 22 year-old small framed inverted triangle, and a college student. I also love 50's style! I do wish I had $1000 to spend on clothes right now, but I'll take the little bit of extra I have from a tax refund. :) As much as I love skirts, our winters are cold and windy here, so I typically wear pants and jeans every day from November to March. Walking too and from classes can be chilly in a skirt or dress even with a coat. Occasionally I'll throw on a skirt for church on Sunday, but that's about it until spring. So for me, dressy and casual pants are must have. Turtle neck sweaters also look great as long as they are fitted. Hope this helps.