Posting some shoe pics and I still have a couple of pairs of black boots on order (despite telling myself I would not do late-season shopping).

Tourguide:
Have been looking for shoes to wear with nude ankle look (skirts, or pants with nude knee hose) for spring and summer, not with winter tights.

Including close-ups of 2 I’m not keeping in case anyone else is looking. Sorry the perspective is weird
#1 is Born Ashleigh tricolor oxford, and I really want to love it but it probably is not going to fit right. This is sz 8, probably too short but too roomy through vamp.
#2 J. Simpson fits more “ladylike” and trim, but the cognac parts are stiff and somewhat cheap-looking and also it isn’t playing well as I thought it might. There is a pink/white version that I thought was just too sweet for me.

#3 - 6 is questions: Frye Courtney in “gray” which is more taupe. 3-5 with sheer nude hose and 6 with off-black. Trying to find a lower-contrast shootie with fit. But, it gaps at the vamp on my low-volume foot.

Pro’s: I still like it—or maybe, I like a lot of things about it; I like being a little cheeky with some heel, and I need a chunky heel vs. tapered, for work; the toe is slightly tapered, though not pointy. I feel like I’m kinda getting an eye for accepting the pale-leg contrast thing and the bootie with sheer hose as being an updated alternative flats, if not too dark.
Con’s: it may be still too flower-potty and worse in a shootie than boote. It’s not nude, is medium-dark, so gives more pale-leg/dark foot contrast than ideal—will still have a more nude version on my list. Chunky foot/thin calf thing may not be my best and I should stick with flats?

So, not just K/R but direction to go in. What are your thoughts on #3 as being an improvement, or good alternative to flats, or not good enough? Focus on a modern loafer? Aspire to something like the Frye but keep looking for a better version? Frye style still too "chunky"?

Any comments and suggestions welcome.