Step 1: Throw everything you own onto your bed. You can start with bags, move onto shoes, then tackle the clothes, but you should take time to analyse each and every piece and discern your attachment to it.
Step 2: Separate your stuff into four piles: keep, sell, donate, trash. You should love what you're hanging back up in your closet and be able to imagine at least two to three outfits with the piece. In order to determine what you should sell, ask yourself this: If you can get almost retail price for the item, would you part with it for money that you can use to buy something better that you love? If the answer is yes, and the item is in good condition, try to sell it. Donate the things that are wearable, but throw away what has stains or holes — you wouldn't feel great about passing that on to someone else.
Image Source: POPSUGAR Photography / Sarah Wasilak