Most Helpful Guys
Take everything out and lay it down, choose anything you want to keep, and sell/donate the rest. Then slowly build your wardrobe back up as you get the money for it.
First off try on the clothes it doesn’t fit, toss it!
Start out with the clothes you never wear.
Most Helpful Girl
Hm. I 'd say keep items that fit you now. If you still like how they look and if they're still usable, that is. Then maybe make a chart of all the activities and events you attend. What takes up most of your time and what kinds of clothes would you spend most of your time in? Then you can start eliminating items that you'd never wear again or you just don't have enough use for. If you have some that you like but can't wear just now, keep one or two outfits just in case. Main thing is to keep the stuff you actually wear on a daily basis and that fit you well.