Dana has had an interesting style evolution. At some point, she had decided that she wanted to upgrade her self-described "t-shirt and jeans" style, so she started trying to add pieces with more interest into her closet. By the time I saw her wardrobe, almost everything had "interest", and therefore nothing worked with anything else. She's also on a tight budget, so she felt bound to all these pieces because they "might work" and she'd have them "just in case" she needed an option without spending money.
After her bed was covered in clothing, we started with the obvious decisions. Things that didn't fit, things that were a gift, things that were worn out all went in the donate pile. I pulled everything to one side that she really loved, that she was excited about when she talked about them to me. This was maybe ten or twelve pieces.
Then we started the long process of evaluating all the "maybe" pieces. It's hard to let go of something that you've held onto with the hope of making it work. It's hard to accept that, actually, it's not going to work. Out went the mud colored pants, out went the awkward-length skirts, out went the tops that only worked with one specific cardigan over them.
Happily, there were also many pieces that did work. Dana just needed an outside pair of eyes to tell her that it was ok to wear x shirt with x pants, and that x dress didn't have to be relegated to dressy events, but could actually be worn to work as well.