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.

The Clarks brand is practically synonymous with comfortable footwear. This company has an amazing way of crafting stylish shoes with next-level support that you can practically live in. And, because ...

All linked products are independently selected by our editors. If you purchase any of these products, we may earn a commission. Depop noted a 39% global increase in searches for Clarks Wallabees this ...