Don't be afraid to let go. Edit your closet and you'll find yourself saying "I have nothing to wear" a lot less. It hurts to get rid of clothes with memories attached, but cleaning out your closet will make way for new memories and save yourself from many headaches.
Here's a checklist for editing your wardrobe:
1. Take out what you don't wear. If you haven't worn it in a year, chances are you probably won't wear it this year. Make a pile and donate it.
2. Tailor pieces you would wear if they fit right. Make a pile of clothes that need to be tailored. Only if you know you'll wear them!
3. Add what you need. Knowing what you really have, go out and make investments that complete your wardrobe.
This is also a good time to get nostalgic, play dress up, and wear heels around the house.