There is absolutely no urgency to this post. I’m trying to decide what to pack for end-of-year travels.

I love my combat boots and am excited that they are back on trend (though I feel they are waning a bit). I’d like to wear them when I visit a friend who lives in a medium-sized city that’s barely South of the Mason-Dixon line. I know the weather will be right, but stylistically, I’m not sure.

I asked friends & family what they thought. Cleveland friend & daughter like them, but the husband/dad predicted people insulting my son “your mom wears combat boots”. My sister in small-town southern Ohio who also spends time in rural W Va thought they look like something our grandmother wore when she was little. (WHAT??) So I can wear them when I see my Cleveland friend, maybe not around my hometown, but I still don’t know about when I visit my friend. He likes my fun maximalism, and he liked the pic in pink pants here (he hasn’t seen others) but he’s also very sensitive to propriety, so if people are eyeing my boots suspiciously, it won’t feel good to him.

Those of you who live in or have recently traveled to the Upper South, please advise!

PS. This is about the boots, not about the outfits here.

UPDATE: I showed sister a better pic of the shoes. Now she thinks the lace legs effect in #5 would be too risqué for where we are from. Really? I was thinking of pairing them with my floral sweater skirt. Again, how do I translate her impression to a mid-sized town in the Upland South?

ETA took out pix of red boots except the one I mentioned in the OP, because the black ones are what I’m really wondering about.