Help me - are these good picks?

I’m a 38-yo woman, live in Chicago, and I’ve lived in converse, chunky Mary Jane’s, and Doc Martins my whole life, and I’m trying to branch out. I’m looking for some everyday and slightly dressier shoes- a pair that I can walk around in during the days for errands and such, and a pair I can put on for brunch/dinners out/theatre.

I’m having a bit of trouble because I have tall feet and narrow heels, so a lot of shoes just don’t fit comfortably. These are what I’ve found that seem to fit what I want, but are comfortable. Thoughts? Are they age-appropriate?

The sneakers are Dr Scholls and the booties are Baretraps.