Thanks to principles I learned from Apartment Therapy's Home Cure, I separated a keep pile from an "outbox" pile. I took no more than a couple seconds for each article of clothing, going with my first instinct to either throw it in the keep pile or toss it in the outbox to be re-evaluated.
After separating clothes between the two categories, I looked over each pile and noticed something. The items in the keep pile were items that 1) I loved, 2) fit, and 3) were in good condition. I also considered my style to be a little tom-boyish, attaching myself to hoodies and jeans and t-shirts and even considering pants as appropriate dress-up attire. But looking over the items in my keep pile, most of them had frilly or feminine details even if the colors were muted and simple. It was a nice indulgence to clean out the items I didn't love, that didn't fit and weren't in good condition. Now I can feel a little more confident that I'll look good in what I pull out of my closet to wear, and I have a little more space to store some of the items that I still "need."