Depends on the climate.
In my opinion hose up look best with brogue style shoes, while scrunched down hose look better with boots.
Though if you are going to wear flashes the hose should alway be up.
No reason why you can't have hose up with boots in colder weather, today I have been wearing hose up because the weather was cold, but I have also been wearing boots to give added grip for pushing a wheelchair. I did not have time to change my footwear before a business meeting later and nobody commented on the boots.