From Princess Diana in the 90s to Kendall Jenner in the 2020s, stylish celebrities have always proven that riding boots aren’t just for the barn.
In 2026, you’re about to see the equestrian staple everywhere, from the runway to the city streets. It is the year of the horse, after all.
Whether you opt for a sleek, pull-on minimalist pair or a wide-calf option with belted accents and hardware, their classic silhouette and knee-high design invites endless styling possibilities.
Tuck some skinny jeans (which are also back and trending) into your riding boots à la Princess Diana or dress up a pair of leggings with a sleek leather pair.
Riding boots aren’t just for the winter. As temps begin to rise, expect to see riding boots paired with asymmetrical midi dresses and flirty mini skirts or styled with knee-high knit socks or patterned tights.
Channel an equestrian chic vibe this spring. Shop the most stylish riding boots from Steve Madden, Michael Kors, DSW, Anthropologie, and more below.
