28 Pairs of Boots to Jumpstart Your Fall Wardrobe

From on-trend knee-highs to non-boring rain boots.

Collage by Ashley Peña

Now that the air is feeling crisp and the leaves are starting to turn, it’s time to put those summer sandals in storage and invest in a fresh pair of fall boots. And this season, there’s a lot to get excited about. Right now, we’re loving knee-highs, from vampy pointed-toe styles to clunkier, ‘90s inspired trouser boots a la Bella Hadid. Another trend we’re seeing: all-over prints. Designers like Paloma Wool, Miista and Proenza Schouler are applying pattern and texture to patent leather, jaquard and velvet — a great way to add an unexpected pop of intrigue to an otherwise straightforward outfit. And who says rainy days need to call for the same old pair of ho-hum wellies? Some of our favorite brands are getting creative with waterproof rubber, fashioning it into glossy, elegant rain boots that are as chic as they are practical. Meanwhile, the best ankle boots of the moment have sculptural heels, elongated toes and unexpected details like shiny hardware or super soft faux fur trim. Check out all of our favorite pairs of the season below.

We only include products that have been independently selected by W's editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.

On-Trend Knee-High Boots

Stylish Rain Boots

Ankle Boots With Personality

Boots With Pattern and Texture