Sperry top siders and Reef flip flops are my typical shoes. Neither is cheap and both are quality. I love the Sperry Gold Cups.
A secret...I put gel inserts in my Sperry's and haven't had them smell, they are so comfortable to walk or stand in, they can be removed and cleaned if needed and the inside of the shoe still looks brand new after a year... Often it is Dr. Scholl's gel inserts, however I also like the 'black' inserts from Dillard's.
Although I will say that I have thrown Sperry's in the washer, to clean the outside. Stuff them with newspaper and put on floor in from of your refrigerator or chest type freezer and they will be dry overnight and look good again.
I would only wear socks with dress shoes...
Give it a try!