Boots and dresses are one fall fashion combo that's never going out of style. As we prepare our fall wardrobes, we're making it a priority to ensure our footwear is in tip-top shape. The good news? Boots don't have to cost a fortune to be stylish. In fact, the majority of our favorite boots that pair well with dresses are under $60. Here are our favorite Amazon-found pairs that'll have you ready for leaf stomping and pumpkin picking. 17 Rich-Looking Boots That Pair Well With Dresses 1. Our Favorite: These Dream Pairs boots are a classic that you can throw on day after day.