not to resurrect an old thread, but has anyone thought about a desert 'chukka' style boot? like THIS

I know it's a classic shoe, and would look great with puttees and a kilt cover, but what about casual wear? And if so, would you go hose up or scrunched down with this lower style boot.

This height seems a bit problematic for me. It seems too low a boot to scrunch hose down, but too high a 'shoe' to go hose up and have it look proper...

or am I just overthinking this?