Our tester wore 10 different styles over the course of a few weeks to determine the most comfortable dress shoes for men.

Boot shafts vary in height and shape, as do their heels. Boots can be made of leather, rubber, shearling, nylon, etc. And they can fulfill different ... of the most common types of boots ...

Opt for a pointed-toe and sleek, architectural wedge à la Bottega Veneta to strut out in an evening little black dress. A pair of knee-high boots paired with your best black mini-dress will give ...

Pair a trouser-inspired skirt with equally classic shoes: It works well with a simple pair of flat sandals to dress it down or pointy toe pumps to dress it up. The entire pairing screams effortless.