You might take a look at Softspots, Clarks, Clarks Indigo (modern) and Clarks Privo (mostly sporty). I search on Zappos.com for comfort shoes and find the look I want.

I wish I could wear Merrell every day, but they are sporty looking, and sadly I can't wear them to weddings...

You might also consider whether you should have an extremely comfortable pair of walking shoes (and good socks) that you can use when your more attractive footwear becomes uncomfortable.

Or consider what I do on urban vacations which include sightseeing followed by a meal in a nice restaurant, which is wear the comfort shoes, and carry dressy, lightweight shoes or sandals which I slip on just before we get to the restaurant. I always have a bag with room for extra items and purchases.