First of all, I have the fussiest feet ever. As in my right foot usually hurts 24/7, even without wearing anything and even in bed. I have low volume feet (no arches) with the tiniest heel and wide-ish in front with bunions. This means YMMV.

Louise et Cie oxfords: These are extremely soft and the metallic look skews gold. I want a cooler more silver metal. The width is probably TTS so a tiny bit narrow for me.

Dansko booties: Dansko clogs generally work for me but the shoes less so. These run a half size short. The front has a bit of a platform so they aren't really a high as labeled.

Dansko oxfords: This style of black oxford reminds me of shoes my grandmother wore in her 80s. These were also a tiny bit short but less so than the Dansko booties. I think the only way I will wear oxfords is if they are in a feminine color or at least not black or brown.

Patent combat boots: Nordstrom said to size up, and these only come in whole sizes. Sizing up made them the most comfortable of the lot. Patent makes them less masculine than your basic combat boot, and these have a zipper on the side. I need to figure out their exact comfort level and whether I would actually wear them or if they would languish on a shelf like the rest of my boots. I will be traveling to Chicago in November, so it would be nice to have wearable boots then.