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To fit the classic profile, a Chelsea boot should also hit a little above the ankle, come with a pull tab in the back, and have a low heel ... and rubbing as the shoes stretched out.

To help you find the perfect fit, we consulted three celebrity and editorial stylists on the best dress shoes for men under $250.

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