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Courtesy of Anthropologie
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.
Kelly & Katie Shry Boot
This polished pair of belted riding boots features a stretchy panel for a comfy fit and a concealed zipper to easily slip them on and off. Available in brown or black, they also come in wide-calf sizes.
Dr. Scholl's Joplin Tall Boot
Boasting a short chunky heel for a little bit of height, these square-toe riding boots lined with memory foam cushioning, deliver the comfort Dr. Scholl's is known for. Choose from three colors.
Steve Madden Sady Boot
Buckle accents adorn the base and top of these mid-calf boots, giving them a subtle motorcycle edge. Available in classic brown or black, they're made from soft, rich leather.
Michael Kors Carson Boot
It's time to bring back the iconic Michael Kors riding boots. This flat pair boasts an almond-shaped silhouette and subtle gold hardware for a touch of tasteful glam.
ASOS Design Conan Pull On Chunky Boots
This pull-on pair of riding boots proves that simplicity always looks chic. With their trendy chunky sole and knee-high design, these boots come in three colors.
Sam Edelman Penny Riding Boot
I can't be the only one who went to college when these two-toned Sam Edelman boots were the shoe. With their traditional equestrian design, these riding boots come in tons of colors and wide-calf sizes.
DREAM PAIRS Women's Knee High Boots
These ultra-minimalist boots are made from stretchy faux leather, with one reviewer raving, "They fit comfortably in every way."
Maeve Buckle-Strap Riding Boots
These shiny leather riding boots are accented with a simple buckle strap. Choose from tan, black, or brown.
Dingo 1969 Vagabond Riding Boots
We predict "it" people everywhere are going to be wearing this specific style. They have a galoshes-inspired shape and a trendy chunky boot that goes with so many outfits.
DREAM PAIRS Women's Wide Calf Knee High Boots
Between their quilted patterns and gold buckle belt straps, these tall boots are extra in all the right ways. They come in several colors and wide-calf sizes.
How We Choose
The E! Insider Shop editors and writers search the internet to find the best products out there. We interview expert sources, comb through customer reviews, and use our own personal experiences to make shopping easier for our readers.
As an editorial team, we independently create content and determine coverage based on research, reporting and what we think our readers would like to read about. The goal of our content is to provide a service and inform readers who are on the hunt for the latest products to help make their life better. Items are sold by retailer, not E!. Pricing and availability are accurate as of publish time.
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