We’ve already made it half way through September, so it should come as no surprise that we are fully into the fall shopping mindset. And with all the street style snaps we’ve been taking in from various Fashion Weeks, we are ready to indulge in a few new pieces for these cooler temps. The first thing on our list? Boots, of course! 

While we can’t quite decide on our favorite silhouette (although tall and slouchy à la Saint Laurent is currently leading the pack), the one thing we are sold on is what to pair them with—and that's a killer midi dress. The midi is undoubtedly this fall’s number one dress shape, and it’s begging to be worn alongside boots of all styles, heel heights, and fabrics this season.

To master this winning combo, be sure to choose a frock with movement, so that it flows over your boot without feeling too heavy. We love an asymmetrical hem (another major trend for fall), crossover styles, or any pieces featuring a daring double slit—all of which bring focus to your boots layered beneath. Whether you lean towards minimalistic, eccentric, or even feminine, we’ve assembled 10 stunning dress and boot pairings to inspire what is sure to be your favorite fall outfit.