Ask yourself if you enjoy each item, one by one
Take the very first item the pile, hold it in front of you and simply listen to what your body says. Chances are you will know instantly if you like wearing that piece of clothing or not.
If you do, create a « yes » pile and throw your item on it and if you don’t, do the opposite.
If you don’t have a clear answer popping out then it is time to rationalize your need. Did you wear that item in the last year, or if it isn’t a seasonable item, during the last six months? If not, you won’t regret not keeping it.
If you did wear it, was it often or not? Unless you truly hate that item but have no choice but to wear it because you don’t have something better I would suggest throwing it away and finding a better replacement.
After going through with this process you should end up three piles, the more you repeat this process the smallest your « no » pile should be. If not then you should reconsider a more thoughtful buying process to reduce your impact on the planet and on your life.
The « no » and the « yes » pile should not move anymore, though I would recommend looking one last time at the items you are sure to keep to see if you didn’t make a bad decision or two. It might happen when you go throw your items a bit too quickly.