Sterling, thank you for posting about this! I'm following along with interest because I've recently told myself it's OK to wear new clothes when I'm just hanging around the house - I don't have to wait to wear them in public. I work at home, so if I don't wear my new stuff at home, I won't have as many opportunities to wear it. Also, I just don't feel good about myself if I spend the day in schlumpy old clothes.
This is my roadblock: When I was growing up, it was strongly instilled in me that anything new or special should be saved "for good" - for rare special occasions, not for everyday.
I've had to confront some deep-seated guilt about breaking that rule, so I've been baby-stepping into it.
I started by wearing the new items that cost the least. I'm still in that zone, but plan to work my way up gradually. I've been overcoming the same issue as you, Sterling, "what if this new item gets dirty or stained?"
I decided to keep an older (but still nice) t-shirt and pants handy that I can quickly change into if I'll be doing something like cleaning that might damage my clothes. As soon as I'm finished with the cleaning or whatever, I return to wearing the newer outfit I was wearing. I like Gigi's idea of aprons, too.
Also, I'm wearing earrings every day, and sometimes a necklace also. That makes me feel pulled-together too.
Anyway, I'm cheering you on, Sterling! Thank you.