Find the right thing to wear
I used to spend hours in my room staring at the closet, rummaging through drawers, asking everyone but the cat what I should wear. And when I got a suggestion, I answered, "No, I can't wear that! It makes me look fat. Choose anything else..."
Then I got to thinking, if it makes me look fat, why keep it? Why keep anything that you won't wear for whatever reason except maybe once a year? So it's time to scale down. Here's how:
Look at every piece of clothing. Sort out 5 tops and 5 bottoms you absolutely love and can't do without. Match shoes and a bag to them - these should fit and look great and be comfortable, too.
Now, everything else has one of three fates: 1) throw it or give it away 2) put it in a box 3) keep it.
Anything you don't love should be thrown out. If you're sure of something, keep it. Stop being overly sentimental - but if you're going to save something for sentimental reasons, at least display it somewhere. Things you're not sure about should go in your "doubtfuls" box. If you find yourself going through the box looking for something within a month, take it out and keep it. Otherwise, it's to be given away.
Now look at what's left. Put away all your summer clothes - it's fall and you don't need them. Put away half of what's left too. Then exchange what's outside for fall clothes inside after a month. You'll have a whole new wardrobe to work with.
Now you have a great set of clothes that you love. Make sure everything matches. If it has nothing to match, go get something or give it away. Put together outfits as you can, but don't be afraid of experimenting.
Pick out clothes the night before. Check the weather and decide what to wear. Set out a whole outfit from top and bottom to shoes and jewelry. Then pick one alternate piece of clothing to wear with it in case the weather is slightly different. For example, if you set out a skirt and top, leave out a coordinating pair of pants too.
In the morning, go with the skirt by default, but if you really really don't want to wear a skirt (too lazy to shave?), go with the pants.
And now with a closet full of clothes you love, you just can't go wrong!
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