I’m a huge fan of juxtaposition in fashion. It is probably my favourite technique for adding currency to my look. Sneakers with a dress or skirt, and a jean jacket with a dress or dressy pants and top combo. Though I personally don’t think I’ll do the elevated flat-form or stompy boot look, I can appreciate (and enjoy) the look on others. I like a more delicate look for my size 9.5s, but honestly it comes down to fear of twisting my ankle or falling since I'm dealing with some gait and balance issues!
Remember, trousers on women, were frowned upon (and even against the law in some places) in the mid 1800’s. The women who challenged the norm and wore them likely did so for reasons beyond comfort and usefulness. I’m sure some women found them avant-guard and fashionable, though the silhouette was likely to be discordant to others.
We all probably have a ‘poison eye’ for something, (or as my son would say ‘it’s not my favourite. ) but for some (many!) things it is a matter of getting past the novelty. I believe it is exposure to different things, including things beyond our comfort zone, that opens us up to the beauty of diversity.
I don’t think you are ‘old-fashioned’ but you might be ‘retro’