Take out all of one thing. Take shoes as an example.
Look at them. Ask yourself
When did you last wear them?
Did you enjoy wearing them?
Were there other opportunities where you could have worn them?
Why didn't you wear them on those occasions?
What could be done to them to make them your 'go to' shoes?
Are they too expensive to keep repairing?
If you don't wear them because they're uncomfortable, they cut, chafe, aggravate your corns or bunions and you don't have to wear them, then get rid. Life's too short for them.
eBay, FaceBook - return them if they're brand new and you kept the receipt.
If they're waiting for repairs, why aren't they at the menders?
Why haven't you bought the polish/Scotchguard/waterproofer/Scuff Stuff/dubbin/special cleaner?
If your heart's not in it, you're procrastinating over them for some reason, then get rid.
If you have to wear them as part of a uniform, you're going to have to experiment with hosiery, padding or toe 'condoms' or find another pair which fits the uniform code and doesn't have you crying by the end of your shift.
If they fit and you don't have to wear them, but they bring back bad memories, they are a faff to look after (suede, fancy buckles, patents etc) you can only wear them with a certain kind of hosiery or padding or you avoid wearing them for whatever reason, then get rid.
Specialised footwear (ski boots, diving flippers etc) which are worn once a year at best, go in their own easily accessible storage area.
Anything you're not going to keep has to go in a black bin bag straight away.
You have to be ruthless and keeping them in your sight line only leaves you guilt tripping yourself over how much money you've spent on them, you haven't worn them 'properly' or you need to give them another chance.
Nope.
You should only keep items you're happy to wear.
And repeat with the next type of clothing.