My checkered Vans are pretty beat up so I'll need new ones.
I finally caved and got "Dad shoes" aka plain ol' black Sketchers that are just easy to put on and take off. The Vans are nice for that too obviously but in Nebraska you tend to need shoes that have a little more traction. I went to a play gym with my toddler earlier this year and nearly left with another dad's pair by accident.
I'm still very much into good old fashioned Chuck Taylors but as I age I feel I need something that offers a little more support. Also, the flimsy canvas tends to make the high tops a tad difficult to put on when you're in a hurry to get out the door. I found a very nice compromise with these Malden Street Chuck Taylor mid-tops that are a bit lower but have more structure around the ankle area, plus I think they just plain look better than the average CT. But now I'm afraid to wear them too often because I'll scuff them or wear them out too quickly.
Long time ago I bought a pair of Vessis (I believe they're a Canadian brand) for running, which I hardly do these days. They look terrible but they're waterproof and are comfortable to wear.