In truth, I cannot say I do this. Right now my wardrobe is really small and there is a lot of purposeful duplication. Consequently, my wardrobe is it currently stands does not lend itself to this type of mental activity.
But I understand exactly what you are asking.
Donating those pieces that you do not wear is certainly a step in the right direction for you. As you clear away the muck, you may have a clearer picture of your wardrobe. Getting your new wider cut pants hemmed may be revolutionary.
If bottoms is your problem, can we try to narrow down the question of why they are your Achilles heel? I'm hearing you don't like wool or heavier fabrication during the winter months, but I feel it has to be more than that. Is it pleating? Is it a feeling of heaviness?