I wear solid-color cotton & poly/cotton kilts to work every day at the Redwood Trading Post, usually with hiking boots or combat boots. In either case, crew length (mid-calf) socks, pulled up, meet the approval of the lassies on the staff and (I assume) the customers.

On the rare day I wear trainers (low athletic shoes), I still wear crew length, pulled up. Again, approved.
Once I did wear shorty socks with trainers, and was quickly informed of their unsuitability.

I rarely wear over-the-calf, mostly as I only have bulky white & ivory wool kilt hose, or plain black.

Seems that the visual bulk of sock + boot/shoe is the key.

But this is California, where shorts & trainers are worn to the opera (God save us!)

-G