There should be four piles during this process: 1) keep, 2) donate 3) repair 4) sell. Regarding repair, if you have a great pair that is too long, take them to Nordstrom and have them hemmed. They will alter things for free that are bought there, and if not will charge you, but they do a great job.Since I'm a fashion rewards member there, they do my alterations for free.
This is going to get too long if I don't cut to the chase. Repeat the process for dresses, tops, shoes and handbags. I would tend to hold on to handbags that are on the bubble, however those have the greatest resale value. When I need cash, I sell a handbag.
Keep: Seeing what you have in your closet makes it easier to get ready in the morning. Invest in some new hangers. The slim, velvet space saving hangers are perfect and reasonable. You can get a huge box of them at Costco. They also sell them at TJ Maxx & Marshalls or Target.
Donate: I'm sure you get the same calls I do from the Cancer Federation, Vietnam Vets and others. You can schedule a pickup with them the next time they call. I like to go for immediate donation so I don't second guess myself. I personally drop them off at the Home of the Sparrow, which is a local women's charity.
Repair: We discussed having things altered/hemmed. Also, time to get the stains out which is a whole other blog subject. Take in your dry cleaning pile.
Sell: This is the fun part that I bet most of you do not take advantage of. I have been doing this for quite a long time. I started out selling my own items in my ebay store, but for a few reasons, I have farmed this out to some bigger fish. I do sell my own designer items that I feel I can do better myself. For designer items that I do not want to sell myself, I have used an ebay consignment shop, therealreal and some local designer resale shops. The average split is 60/40, with you getting the 60%. They do all the work, and in many cases they will send you a pre-paid label to ship the items to them. For mid brands like Ann Taylor, Banana Republic or Gap I also use a consignment shop or a chain like Clothes Mentor. Clothes Mentor and Platos Closet (for juniors brands like Ambercrombie, Forver 21) are national chains that will give you cash on the spot for your items. I also just tried using TWICE, an online reseller that I saw advertised on Facebook. The items must be clean and in excellent condition. You don't get rich doing any of these, but it's a nice alternative to donating. I spend a lot of money on clothes and love to donate to a worthy cause, but many times when I splurge on an item I do so knowing that I will be selling it in the future. Sometimes I am able to get more than I paid for the item. For your designer items, saving original tags and receipts helps increase the resale value.
One last alternative is to host a SWAP Party with your neighbors and friends. I've read about these and they sound like fun, but I'd always feel sorry for the girl that nobody wants to swap with. Too much stress. But if you have a group of friends with similar taste and sizes, this could work well for you.
When your done with cleaning out your clothes closet, make a list of the items that you feel are lacking in your wardrobe and use some of your profits to fund the purchases. Be smart about adding new items, the trendy items need to be deals, and invest in the classics or items that you will wear often.