How to have a Winning Wardrobe

Purge ruthlessly.
Keep only those pieces that you absolutely love and that you currently wear on a regular basis. If something doesn’t fit, has holes or stains, is out of season, or you just really don’t like it anymore, it needs to come out.
Determine each item’s fate. Just because it comes out right now doesn’t mean you have to throw it out or send it to Goodwill. If you’re anything like me, you probably have clothes in a variety of sizes, some of which you may still really like and hope to fit into again. Store a bin of “skinny clothes” to pull out - when you lose the weight.
Invest in great hangers. It is such a simple thing, but I found that buying a limited quantity of really nice hangers was the best motivation to finally weed out everything I didn’t love. It really wasn’t a huge investment but psychologically it made all the difference. And frankly, even inexpensive clothes seem luxurious when hanging on nice hangers.
Minimize your losses. Clothes & accessories that are in good shape can be brought to a consignment shop  or sold via Craigslist, eBay, Facebook, or garage sale.
Make it easy to keep things in order. Set up a no-fail system that is simple to maintain. I have clearly labeled baskets for the things that are hard to fold–bras, panties, swimwear, socks, pajamas, & accessories. I love keeping the laundry hamper in my closet as well–it makes sorting laundry so much simpler!
Once you’ve managed to pare your closet down to the bare minimum and have kept the pieces you truly love, keep it that way! When buying something new, choose quality over quantity. Resist the urge to buy something simply because it is on sale. You are always better off buying ONE piece that you love than TEN items that are just okay.
Re-evaluate regularly. It is a good idea to re-assess, re-sort, and re-evaluate your closet every few months. Once a season double check to make sure that your items are still in good shape, that they still fit, and that they are free of stains & holes. If necessary, pull seasonal items out of storage to add to the rotation, and store any items that are no longer seasonally appropriate.