Take every item of clothing you own out of your closet. Lay the pieces on the bed, the dresser top, the chairs — do whatever you can to get everything in a place where you can actually see it. Include scarves, shoes and other accessories.
Arrange the clothing by color. Because winter clothes usually lean to solids rather than prints and deeper colors of the palette, you will most probably have piles of blues, browns, blacks, purples and reds.
Evaluate each color pile and decide what items need to be replaced and what you are missing. You may have a two-piece blue suit with a perfectly good jacket accompanied by a worn-out skirt. Decide whether the jacket can be worn with anything else in your wardrobe. You might come up with a great look by pairing it with a lightweight sweater you already own and wearing the jacket and sweater with jeans. If you own a great pair of purple pants but have nothing to wear with them, make a note to look for a top — but before you do so, look through the rest of your clothes and find one or two other items you could wear with that new top. For example, a purple-, black- and white-striped shirt could also be worn with black pants.
Budget the amount you can spend on new winter clothes by analyzing your wardrobe notes and prioritizing what you need. Estimate the amount you would expect to pay for each item you need — and stop when the amount you have budgeted runs out. Decide what accessories might add a great deal of punch to your wardrobe at little cost and see how well those might fit into the budget, even at the expense of eliminating a larger item.