My wife and I are close friends with another couple. I am out to them as of maybe 6 months ago. The four of us have been out to a bar with me dressed. We have known them for 30 years.
The wife of the couple, while not masculine or butch, is definitely not a girly girl, and is on the plus-size end of things. My wife (who is not plus-sized) and I both shop at a local thrift store, with me sometimes dressed and sometimes not, and we have been telling the friend about our finds.
Last week she called me up and said "My birthday's coming up in a few weeks. For my birthday, I'd like you to take me shopping at [Thrift Store]". Of course I was thrilled. Bottom line -- she's picking me up Thursday morning to hit that store which is local, and another in a town about 15 miles away. She came over today and mentioned that she assumed I'd be dressed for the outing.
So now I have to decide whether to wear a black denim skirt, which I love, or black denim capris, which is, of course, the kind of thing most GGs will be wearing. I've got nice purple toenail polish to wear with my slightly heeled sandals, and a new (to me) green top that I got from that local store.