Stacy Adams Chelsea Boot
These boots look uncomfortable but the sole is very soft and supportive. They are easy to slide on and off.
I love the way this color shoe pops with dark jeans. You can even pair them with a less formal suit.
New Balance 527 V1 Sneaker
New Balance is known for comfort. These shoes are great for a long day in the park. They come in several different colors.
Converse Chuck Taylor Boot
My personal faves. Converse took it’s classic sneaker and gave it a boot look.