Heading to Prague for a few days end of September
Usually for city breaks I just wear the merrells and get on with it. Only Prague is as I understand it, more stylish/smart casual
City breaks for us are out early morning, sight see, sight see, sight see, then early dinner wherever we collapse around 5 , and back to apartment for a nightcap and crash till we do it again the next day :) ( 60's ) . So never needed more than our day clothes. This trip we have two places we need to look a tad smarter - not sight seeing clothes - but we are still doing the underseat bag so looking for help in finding a pair of shoes which will go day to evening and be able to cope with 20k steps on cobbles a day . For the more dressy up occasions it will be trousers for me . Just dont want to be walking into a half decent restaurant and concert hall wearing obvious walking boots