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

To help you find the perfect fit, we consulted three celebrity and editorial stylists, all with years of experience in the fashion industry, on the best dress shoes for men under $250.

We're especially fond of the Timberland Premium 6-inch Boot for its timeless appeal and the Red Wing Shoes ... men or perhaps something a little more dressy, like the best men's leather dress ...

But both wore Gucci's new horsebit leather ankle boots from the brand's spring 2025 ... from the pack of actors wearing traditional dress shoes. The 82nd Golden Globe Awards was held at the ...