How to Wear Boots With Dresses Like a Style Influencer This Fall

All year long, I look forward to dress-and-boots season—and to solving the inevitable question of how to wear boots with dresses, of course. I love breezy summer style as much as the next fashion editor (more, probably—I am a Cancer, after all), but there’s just something about a delicate gown styled with tough, knee-high boots—or ankle boots, or moto boots, or cowboy boots—that strikes the perfect juxtaposition.

The traditional fall combination is beloved by baddies and cool girls because of the effortlessly stylish aesthetic it aces time and again. It’s throw-on-and-go style at the highest percentile. In fact, I’d go as far as to say that if you decide to outfit-repeat only one look this fall, it should be this one. Because a good dress-and-boot outfit will never let you down, no matter where you’re headed. Below, peruse the most stylish ways to wear boots with dresses.

How to wear knee-high boots with a dress

The utility trend, as cosigned by Jennifer Lopez and Kendall Jenner, has yet to reach its peak. The look, which combines elements like earthy fabrics, breast pockets, and funnel necks, will continue well into fall, paired with knee-high boots and luxe leather bags.

How to wear ankle boots with a dress

Thanks to high-end labels like Hermès, burgundy boots are on every fashion girl’s wishlist this season. Use them for expert color-blocking by styling them with an espresso midi dress and a smattering of wine-colored accessories.

How to wear slouchy noots with a dress

Eyelet-midi-dress summer has officially turned to eyelet-midi-dress fall. The only difference between the two is longer sleeves and a pair of boho boots. Add a dangling pendant necklace for some extra intrigue, and you’re ready for a concert or drinks with the girls.

How to wear over-the-knee boots with a dress

Now this is my kind of fall ’fit. Add a distinct punk-rock flavor to your frilliest mini by throwing on a boxy leather jacket and over-the-knee boots, plus trendy shield sunnies for even more edge.

How to wear suede boots with a dress

Suede hasn’t seen such a promising fall season since the early 2010s. In the coming months, you’ll see the suede-boot-floral-dress combination too many times to count. Finish with a fringe jacket to keep the aesthetic feeling fresh.

How to wear moto boots with a dress

Motorcycle boots are the cool girl’s bread and butter. Their innate edginess touches every piece they’re paired with, but in my opinion, their powers are best exhibited when styled with a bold, printed dress and a matching bomber.

How to Wear Cowboy Boots With a Dress

Cowboy boots pop, even with a monochromatic look. Style it intentionally with an opposing hue to make the statement shoe stand out even more.