"So I wear a softshell that looks less like an outdoor jacket and more like casual wear at a glance for milder weather. Versatile, too."
I bought a new Arc'teryx Gamma jacket back in the mid 90's at a seconds store for $125 and finally wore it out enough that what little vanity remains in me at this point in my life whispered softly in my ear, "C'mon, you old cheepskate, shell out and stop embarrassing your wife". Serendipitously, at about that time some BPLer, Delmar, I believe, posted that Costco was selling the latest Gamma for $140, so I caved and picked one up. Now I'm set for another 15 years or so and my wife has a smile on her face when we step out, instead of a sneer. ;0)
The old Gamma was passed on to a local charity where someone even less concerned about appearances will no doubt get at least another 5 years of functional use out of it, as I had all the zippers replaced under warranty before I let it go.
Like many who have posted, I am sceptical about trying to use my backpacking clothing, which is quite specialized, in urban settings. They are 2 different environments that require different approaches to dressing oneself. My 2 cents.