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
BERLIN, GERMANY – JULY 4: Lea Jouana is seen wearing a beige cotton button front mini shirt dress with a fitted waist from Zara; dark brown leather pointed toe knee high boots from NA-KD; a small dark brown woven top handle raffia bag from Mango; gold hoop earrings and gold rings; oversized square tortoiseshell frame sunglasses with brown tinted lenses from VEHLA during the Berlin Fashion Week Spring/Summer 2026 on July 4, 2026 in Berlin, Germany. (Photo by Moritz Scholz/Getty Images)Moritz Scholz/Getty Images
