Long story short: I stopped upkeep on my clothes about 3-4 years ago. I was expecting to get pregnant, and well, it took longer than planned. After that I knew we would be buying a house to make room for the new baby and we were saving for a down-payment. So I stopped buying clothes. I didn't want to buy something that wouldn't fit once I got pregnant, and I didn't want to spend money that should be saved to get us a better house. Jump to now, the baby is 6-months old and we moved into the house last month. Yay.

My closet is a mess. I'm wearing the small handful of clothes that fit me right now that were too essential to put in storage while we were moving. Some of it is still maternity. Most of it is several years old.

I'm dealing surprisingly well with a much smaller wardrobe than I ever thought I could do. Do I embrace the new minimalist lifestyle?

The rest of my clothe are (1) too small, (2) didn't fit that well to begin with, or (3) old and worn out. I need someone to give me permission to throw them all out and start over. 

P.S. How do you start over?
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Update:
First, thank you everyone for the encouragement and wisdom. Here is what I did. I went through my boxed up wardrobe, and anything that didn't fit and wasn't a high-quality piece went in the donate box. That left me with one reasonable box of really nice stuff to store just in case ( just in case I spontaneously drop a dress size).
Next I went shopping. I put in an order online at my favorite store (Banana Republic) for basically a work capsule. Everything matches *and* fits with existing stuff I own. Then I took a trip to the mall. I brought my mother to help with they baby and bought a few dresses (washable) and a nice work shirt.
I'm not completely done. I still need to replace some of my around the house clothes that are literally in shreds, but dressing for work is so much easier now.
The best part is I feel so much better! I feel like my old self again. I feel like I look great. No more shabby "just getting by for now".
Seriously, thank you!