Three months have passed and I finished my first round of wearing Thirty Items for Three Months. This has been one of the most successful things I've tried over the years (probably along with stopping shampoo).
There's the psychological and the practical side of the challenge. From both sides, there are pros and cons. There's the fear of not having enough clothes, and the practical challenge of actually not having enough clothes (which varies depending on your climate and lifestyle). There's the wondrous freedom of not having to choose what to wear, and then there's the practical freedom of having a very manageable, simple closet.
What I like about the challenge is that it limits you temporarily, so my big fear (and practical concerns) are minimized. At the same time, I experience many of the freedoms.
I've also felt emancipated-- at least a bit-- from those deeper fears of not having enough or of not having something because I gave it away. As a result I've been able to give away much of my clothes and Noah's clothes. Giving away Noah's clothes felt like letting go of his babyhood (yes, I'm melodramatic), but also letting go of the fear of wasting money or not having enough resources if a new baby joins our family. This makes sense for us because we're moving and not taking much with us. It may also make sense for you if you don't have basement or other out-of-the-way storage. And we gained a surprising relationship with our downstairs neighbors by giving them a huge amount of clothes for their tiny son.
There were quite a few things in my 30 things that I didn't wear for much of the three months-- mainly because my size is still in flux and my belt broke, meaning my two pairs of work trousers were out of commission. Today, I'll choose a new set of items for the next three months.