The Ultimate Guide to What Boots to Wear With Dresses

In case you missed it, we’ve officially entered the fall. With this period comes a whole new set of things to be excited about—especially for the fashion set. Autumn is the time when many people decide to get serious about rebooting their closets. For some, that looks like investing in a few trends, while others do a total closet cleanout. While the latter option, is noble, the start of the new season can usher in added pressures to “ditch” everything old and bring in the new. And while there’s nothing wrong with wanting to replace a few worn-down staples, the idea that you should buy an entire new wardrobe every season is unsustainable (both for the planet and your wallet). It’s crucial to find new ways to style items you already own in a way that adheres to the autumn aesthetic.

But if you’re unsure what pieces lend themselves to doing just that, let us give you one place to start: your dresses. As counterintuitive as it might seem that a dress worn at the height of the summer could transition into the fall, it’s indeed possible. In order to prove that point, we scoured the internet to find outfits that show how to wear boots with dresses. After hours of research, we narrowed down the 10 best boots to pair with every type of dress. Plus, we shopped out the best boots on the market based on longevity, price point, quality, and editorial perspective. Consider this your masterclass in making last season’s dresses feel relevant through styling this season.