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Stylmartin Indian fit the bill: https://the-cafe-racer.com/stylmartin-indian-motorcycle-boots-brown
I wear mine with either type of sock. The soles aren't super stiff or anything and they're incredibly hard wearing.
Haven't seen the brown irl, but the black is nice, so I assume the brown would be too.
Candidates for a waterproof boot with a decent sole, vibram perhaps, compatible with a thinner office sock rather than a thicker walking sock?
Am wearing DM boots in the current weather to get to work but they aren't great with a thinner sock.