The Gigi Pant
A good pair of leggings is a necessity. The Gigi Pant from the J Crew factory store is a more affordable dupe for the J Crew Pixi pant which retails for $98. These are made with a material that is thicker than your average legging, but softer than jeans, with the added bonus of a slimming effect. The Gigi pant will save you at least $30, but still deliver the quality you need. https://factory.jcrew.com/womens-clothing/knits_te...
Quilted Zip-Front Vest
Quilted vests can often run for more than $100, but this one from Old Navy looks the part at a much cheaper price. This is the perfect piece to layer over long-sleeves or plaid shirts. http://oldnavy.gap.com/browse/product.do?cid=98796...
Bean Boots
The bean boot by L.L. Bean has been a popular fall staple for a while, and they are here to stay. They are well worth their price for the quality and usefulness of this shoe. These work in the rain and snow, but also look great throughout the winter styled with tucked-in jeans and a quilted vest. http://www.llbean.com/llb/shop/35477?feat=506708-G...
Shaggy Faux Fur Vest
The fur vest has also been a staple for a while, and if you never got around to taking the plunge to purchase one, it's better late than never. Fur vests are cozy, yet chic and can be styled in a number of ways. This one from Forever 21 is very affordable and can be paired with jeans or leggings and a cute top for a night out. http://www.forever21.com/Product/Product.aspx?Br=F...