While I've now migrated into wanting synthetic, lightweight hiking shoes rather than traditional leather boots, I have to admit I still really like the look of hiking boots. I'd wear them around town, even if I'm less interested in wearing them on long hiking trips anymore. And there are some, especially if I'm going to be seeing lots of rain or snow (or the possibility of it) along with off-trail rambling, that I wouldn't mind wearing, usually highly engineered ones that are lightweight.
The Perfekt series by Meindl, especially the light hikers or vented light hikers, may be the best bet. I also like some by Danner; the Extroverts have the look of a traditional boot while really being a synthetic ankle-supporting hiking shoe, but the Nobos and the Mt. Defiance, and the 452s are all Danner boots that I wouldn't mind owning, and in which I'd probably hike.
I always tell people that I don't get hiking clothes to be Backcountry Chic, but let's face it; everyone likes to wear stuff that they like the look of, and most people like to broadcast their tastes and preferences via their look at times. I love hiking boots; I've worn them off and on as simply shoes ever since I was in high school many years ago. I'd do it again.
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