My go to shoes for casual wear and work
Merrel MOAB
>lightweight
>breathable
>comfy
>suitable for casual wear
>not a lot of ankle support
>not a lot of waterproofing
If you want something you can run in, these or something similar might be a good bet. I don't wear jeans, but I think they look presentable with khaki, olive, or grey work pants.
Asolo Valley
>great support
>light enough, you could run in these if you needed to
>good water resistance
>comfy
>suitable for all seasons
Great ankle height hiking boot. As far as fashion goes, same as above, depending on which color scheme.
Austrian meme boots
>cheap
>can be waterproofed easily, like most all leather boots
>high upper allows decent ankle support
>needs aftermarket insoles for arch support
>good luck running in these, at least at a fast pace
They can be polished up to go with just about anything, so long as your pants cover the upper. Otherwise you look like a total autist. I wear these for my retail job, where I spend the better part of my shift standing. Took some breaking in to become wearable, but at this point they aren't bad.
Red Wing 2406
>steel toe
>welted sole
>comfy as fuck, excellent support all around
>can be waterproofed
>heavy, but compared to other work boots, respectable
>not well suited for running, but again, if you want to, you can for a few dozen yards
I wear these daily for machine shop training. Very easy on the feet, very well constructed. Red leather goes with jeans pretty well. Definitely doesn't stick out like black tactishit with tons of zips and shit on it.
All of these are expensive (except for the meme boots), but shoes aren't something to cheap out on. The first two I listed were bought by my mother three and four years ago, which speaks to their quality, seeing as they are still in great shape.