Gaylene, I just love how you always distill these things so well. You're absolutely right. I worked some kind of office job literally from the time I was 16 until I became self-employed, and even during a little bit of my self-employment time (temped in design firms, etc.). I always have a little bit of that "what if I need this?" mentality I learned from my mom. The truth is, even IF I ever had to show up in an office for some reason (and I deal with plenty of professionals in architecture and design firms), I can certainly put together a really polished, professional, yet creative outfit from the other items in my closet.

Claire, well-said. Clothes that guilt-trip me should go. I know this to be true, yet here I am looking to you all for validation. So interesting that I am such an independent person, yet I have to come to you all to ask permission to get rid of something that *I* don't necessarily find useful, because I think it *should* be!

Hmm, these two jackets seem very similar to one another. Maybe you can let go of one? At first I thought I liked the second one, but I think the first one looks a bit more now, so I''d keep that one.

Such a great discussion. I think it is precisely these items that I have most trouble letting go of, also. Great quality. Decent fit. Could fill a gap. But DO they? And even if that occasion came up -- you'd probably want something new!

Off they go to Dress for Success.