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You can do this by yourself or with a good friend - who will be HONEST with you.
1. First, take everything out of your closet and try every piece on.
2. Make 3 piles - Mend, Swap/Donate/Trash, Keep.
3. Once you have tried on everything, go to your KEEP pile. Anything you haven't worn in two years or more, put into the swap/donate pile (unless it's a timeless piece like a dress that you would wear only on very special occasions).
4. Now start mixing and matching tops and bottoms (and shoes!) in ways you might not have thought about before. Even if you think it won't work, try it anyway. This is a good time to bring out your accessories. When you find a "look" or an outfit that "works", take a picture of it. (If you have a friend or a tripod, get a pic of you IN the outfit. You can also play with your hair - some tops look better with hair up or away from your face, while others look better with your hair down.) At some point, load the pics onto your computer, shrink the pics so you can fit maybe 4-6 shots on a page (landscape works best) and print it out on plain paper. Keep this near or in your closet -maybe on your wall.
* about neutrals - Neutrals with neutrals work well together, and can be brightened up with brighter accessories. For example, black pants with a neon or really bright top can look a little 90s, or look like you are wearing a uniform. But black pants with a cream colored top and a kelly green belt or turquoise scarf can be stunning. I also think that muted colors like olive green, slate blue, or mauve can look great with neutrals. Just play around.
5. Once you've gone through all of your KEEP pile, organize your closet. I prefer to keep dresses on one rack, then pants, then skirts. On the other rack are tops. I organize first by sleeve length - tanks, short sleeve, long, then by color. Some people organize by color and THEN go by sleeve length. THIS SOUNDS TIME CONSUMING AND OCD - but it helps on a day when you have little time to pull an outfit together. I like to wrap scarves or necklaces on the hangar of particular tops or dresses that absolutely define the outfit.
6. Once you know what you have, you can identify "holes" in your wardrobe. For example, do you need a pair of dressy black pants? Perhaps a casual dress? Maybe a few accessories? What about underwear? Do you have the right size/style/coverage for your outfits? Might be a good tie time to get a bra fitting - many women wear the wrong size. When you have the time/money, this is the list you take shopping.
7. You can also have swap parties with your friends. One person's "never worn because it's too bright and too long tunic" may be another person's "absolutely gorgeous top that goes great with my skinny jeans". Bring anything you don't wear or like or that doesn't fit - clothes, shoes, accessories - you'd be amazed what other treasures are in other people's closets.
8. What doesn't get discovered by someone else can go straight to Goodwill or the Salvation army or a women's shelter. Also, there are organizations that supply unemployed or underemployed women (many who are in poverty, or homeless or just returning to the workforce) with new & used good-condition suits and workwear to wear to an interview.
Also remember:
- get items that need new buttons or hems or cleaning to the tailor/cleaners - sometimes a small fix can transform how something looks on you
- trash anything that is ratted, holey, ripped or otherwise unwearable.
Good luck, and have fun with it!
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