1. Schedule TIME. Don’t rush this process. Give yourself a full day, maybe even a weekend. Sort through each piece with a critical eye. Take everything out of the closet. Try things on! The point is to create a closet full of items you truly love, not just tolerate. And love takes time.
2. Bring a Friend. And not your agreeable “yes” friend. Your honest, ruthless friend (and preferably one who shows up with champagne). You want someone there who will give you the hard truth on the items you own. She'll tell you what's flattering and more importantly, what's not.
3. BUT Trust Yourself. I have pieces of clothing that aren’t necessarily the most flattering pieces, but I love them. Friends don’t always understand these pieces and that’s okay. At the end of the day, this is about your own personal style. If you really love something, keep it. Just make sure you wear it.
4. Make 4 Piles. Keep, Edit, Donate, and Maybe. Keep the items you love, fit well, and are in good condition. Edit pieces that need to be tailored, hemmed, resoled, etc. (and actually take them to be fixed!). Donate everything else. Haven’t worn it in over a year? Get rid of it. The more you donate, the more room you have for items you feel great in. Give someone else the opportunity to love an item you now feel so-so about. Look into non-profits like The Salvation Army, Goodwill, Dress for Success as well as women’s shelters for places in need of clothing.
The Maybe pile is not an essential, but if you have hoarding tendencies, it makes letting go easier. Sometimes an item is hard to get rid of until you’ve gone through the entire process. A maybe pile lets you safely put items aside and reassess after you’ve gone through your entire closet and you realize you don’t need 7 striped shirts (guilty). Most of those maybe items will end up in the donate pile when you realize how many other amazing and better fitting pieces you own (and probably forgot about).
6. Don’t Let Sentimentality Own Your Choices. We all have items in our closets that we never wear but we keep because it reminds us of a certain event. Unless it’s your grandma’s vintage wedding dress or something truly special, get rid of it. How many college sweatshirts and fun run tees do we really need?
7. Be a Better Shopper. Now that you have a closet filled with items that fit, are flattering, and you love, keep it that way! Stop buying clothing simply because they're on sale or affordable. It’s better to save up for quality items that work for your figure and your life than buy a bunch of cheap things that sort of work. Pay attention to what ended up in the donate pile. Try and avoid the same pitfalls.
Good luck, have fun, and enjoy your new curated closet!