On a recent family trip to the Berkshires, I popped into a tiny boutique in Great Barrington. I saw the cutest sneakers that looked insanely comfortable: Bensimon Shoes! Found! Piperlime is having a sale on their classic for just $29.99 with free shipping and free returns.
They have a couple of simple styles and a million colors. Reviews online say they are just as comfortable as they look. Can't wait for mine to arrive in the mail. They were too pricey at the moment but I made a note to check online.