Pull EVERYTHING out and organize it by size. Starting with what you wear now, try on everything. If it fits weird or has stains, get rid of it. If it is out of season, fold it up and set it aside.
If the clothes are smaller sizes, go through them and get rid of anything you don't like or is excessively trendy. Remember , what you lived and was on trend a couple years ago, won't be what you love and on trend a year from now.
Keep the clothes you wear now in your closet and put away all seasonal and smaller sizes into storage.
Without knowing how big your closet is or it's set up I will suggest measuring it and ordering an organizer or expander. They're $10 on amazon, and they will give you an extra rail to hang clothes from.
For shoes I would start buying plastic shoe boxes to keep the organized. Some people like using shoe racks, and that's cool too, but get anything that's on your floor organized and under control.
Does your closet have a shelf? If so, is it occupied? I keep all my bras, underwear and camis/tanks in 3 separate bins on the top of my closet. Once I get a 4th bin, my socks will be there too.
If you have a shelf, consider how best to use this space; maybe put those blankets up here so you can fit more clothes under the bed?
I'd get rid of the too big drawers. Sell them on eBay or Craigslist so you can recoup some money. If an organizing solution is causing more disorganization, get rid of it.
What is your furniture situation? Do you have a dresser or chest of drawers?
Consider going through those and getting rid of stuff so you have more room.
Honestly, the biggest suggestion I have is to sit down and honestly think about where you are right this very minute with your weight. Can you honestly say you are doing EVERYTHING you can do to lose weight? Can you say that you are confident you will fit in to some of these clothes in the next year? If not, get rid of them. If you need suits for work, don't get rid of those, but jeans and t shirts can be replaced relatively cheaply.
I had to do this with myself a couple years ago because I was in a similar situation and had a huge wardrobe from size 6-22. I ended up getting rid of all but a couple smaller shirts ( I think I have 2 mediums and a 3-4 Larges left) and 1 pair of pants in almost every size (I have 1 16, 2 14s, 1 10) and a couple smaller dresses. Everything fits into 1 space saver bag.
It was important for me to do this not only so I had more storage space, but because it's important to be honest with yourself about what your short term goals are.
Good luck!
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