In my first bit of tips for developing your style I talked about giving your closet a good clean out. It can really help you learn a lot about yourself, but it's great to start with a clean slate too. Of course, most of us (myself definitely included) have trouble with figuring out what to keep and what to let go. Getting rid of anything you haven't worn in the last year is pretty obvious, and fairly easy to do. What about those pieces we wear only every few months?
A great place to start is to pull out all of the pieces in your closet that's you don't wear often and lay them out. Out of that pile you can put anything back into your closet that you really might need in the next few months. For example, I always keep a pair of professional pants in my closet for interviews or jobs I might need them for. At one point I had a couple pairs of these, but it isn't often I actually need them, so I only kept the best fitting pair and got rid of the rest.
Next, pull out any sentimental pieces. I rarely wear t-shirts, but last year when we were getting ready to move I realized I had a huge stack of t-shirts. A lot were "sentimental" so I decided to let myself keep a couple, but get rid of any that weren't sentimental and I didn't absolutely love. It's okay to keep a few things that remind you of special times! But if you never actualy wear it, then think about putting it into storage, or at least out of the way.
You also want to keep things that you really feel amazing wearing. I have a few dresses that I don't wear often but I do feel great in when I do, so I let myself hang onto a couple of those. But if you have any that you love, but never wear even when that special occassion does come up (I've been guilty of that plenty of times), then it may be time to let it go.
What's left? Probably still a little bit at least. What is left you might still feel a little on edge about getting rid of, I know, I've been there. What I always do with these things is swap them! You can swap with a friend, host a swap party, or take them to a consignment store. We have a bunch of Plato's Closetstores around, which pay you on the spot for your unwated clothing that's in good condition. I like to take that leftover stuff in and put whatever money I get from it towards picking out a few new things. It's a lot easier to let go of that rarely worn stuff when you have new things to be excited about!
Also, feel free to put on "Let it Go" while you do your sorting to get you in the mood:)
PS. I'm in no way affiliated with Plato's Closet, they're just a company I've been going to for a while and thought might be helpful for you guys. If you guys know any similar places, please share!