Anna: I've been toying with the idea of a gray boot for a couple of years. Love this look when I see it on others!
Glory: thanks for asking me to post pics, that was instructive for me. In answer to your question, I wear the Fryes quite a lot--I love breaking up a black outfit with them. The cognac ones not so much BUT when I do wear them (eg with black pants, with a cognac belt) my happiness factor is extremely high. Did you mean the olive SE Pippen? That is a super cute color.
Suz, good point. My #1 style goal when entering the forum was to wean myself away from black tees. I've definitely done that (though I wore one today just for fun). When Angie was talking today about no black shoes, I felt this nudge (from myself, not Angie) to think of black booties the way I think of black tees. Your explanation is helping me see that they may not be in the same category for me.
Lynn, I think I needed you today! Sometimes enabling is just encouragement!
Angie, burgundy would be a great color for me! One favorite style memory is burgundy penny loafers in the 80s. And thanks for permission to wear black!
Donna, I can't imagine the color adventure with graying hair! I love all of your suggestions. Whatever I get, it will be dark...gunmetal, espresso, yum!