8. Greats Brand “Hirsh”
Before anyone questions this pick, I’ve included it because of the running sole that was used. I’m a big fan of what Greats is doing in the industry, and this is my favorite model from them. Cole Haan changed the game with the Lunargrand, and no other brand has been able to duplicate that sneaker/boot fusion like Greats did with this classic dessert chukka sneaker. As I’ve gotten older, I’ve added some diversity to my footwear rotation, and this pair offers the best of both worlds when it comes to sneakers and boots.