It's one of those rare days that I need transitional shoes-and help from the collective YLF wisdom! Suz my foot twin, please chime in!

The shoes: Currently I own 3 pairs of non sneaker transitional shoes- shown below. They're all mules, because I have extremely narrow heels. The black I have a hard time walking in, and have heel damage. Debating repair or passing on. The mustard I Tarragoed with cognac but still aren't right (no other mustard in wardrobe). They feel too plain or too casual or something. The tan are my favorites, but too short for my feet. Maybe my feet got longer. May hunt on eBay for bigger size.

The feet: 9AA with 6A heels. High arch and instep. Transitional shoes come right off my heels and rub badly as I do. I've tried All The Inserts, no help :/

The context: work (biz casual to dressier) and weekend, 50-60 degree weather. Usually a couple days in April and November. Often those days have rain. PUPY (potential uses per year) value probably 20 max. Under normal circumstances, only about 2 or 3 of those would be non work days. Temps below 50 I wear boots/booties, over 60 always sandals.

Seeking: streamlined feminine flat-2.5 inch or so shoes to wear with trousers and possibly longer skirts. Lowish vamp, pointyish or almond toes, nothing cluttery looking. Could use black and cognac. I do not want to wear sneakers of any sort outside of exercise. I don't care if they're trendy- they make me feel like a 12 y/o boy.

Considering: knit flats (would they hold up in rain?), simple loafers like the Emmelines, slingbacks, shoes with elastic backs. I had some Trotters pumps that worked somewhat better than most a few years ago.

Other ideas? Good brands to check?
What does your non sneaker transitional shoe wardrobe look like and how much do you wear them?