You can never go wrong with a pair of Chelsea Boots ($120), especially from Steve Madden. They’re designed with a round toe, chunky block heel, lug sole, and pull tabs for easy on-, off- maneuvering.

Promising review: "LOVE THESE FLIP-FLOPS! I have Clarks boots and always thought they were one of the most comfortable pairs of boots I've owned. When I saw they made flip-flops I used the Try Before ...