Clothing is not a "one size fits all" (pun intended) issue. You have a juxtaposition of life style, space and quantity of items.
If you work in a downtown office building or a sales job you may need a lot of suit type dress clothes. If you farm or drive a dump truck you need jeans. If you play in an orchestra or go to a lot of social events, you may need evening clothes. Many of us don't, and don't. You will have to translate some of that into the equivalent of women's clothing.
In his blog, Brooks Palmer indicates that he basically asks his clients questions like Do you like this, will you wear it, or can you let it go. One of his more fun questions (which most folks on this board don't agree with asking) is: "If this was food, would you eat it?" A little different way to identify clothing that is meaningful to you. I would guess that if you have a lot of clothes, you could make a first pass through looking for worn things, things that no longer fit and things that you totally abhor but are keeping because they were bargains. (Like some of my 20 year old neckties from when I wore suits.)
You would then be in a much better position to make another sorting run thinking about your work, casual and social clothing needs and the space you have to store them.