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Web best dresses to wear with cowboy boots to weddings. Web we’re seeing more brides wearing short wedding dresses with boots, but that could simply be two reasons: 1) it is for a summer wedding with hot and humid weather, and 2) they really want to show. We’ve rounded up some of our favorites to go with rustic and country. Web finding the perfect pair of cowboy boots to go with your wedding dress can be like trying to find a need in a hay stack, it’s going to take some time! It’s important for the color of the boots to complement whatever dress you.