I Found Tall Riding Boots for Non–Horse Girls

These are waterproof, which is a win, but the grooves and stitching detailing around the outsole felt edgier than I wanted. The heel is around 1.2 inches, which is right around the sweet spot, but the blocky shape of the heel felt off to me. I think these are a solid pick if you want black boots that don’t necessarily have anobvious equestrian look, but I felt there might be a better option out there for me.

These are a pull-on style, which I actually didn’t mind. But beware: The shaft is snug and doesn’t have much give. I tested out the dark hickory leather color, which has a genuine calf-hair upper and a leather rounded toe. I absolutely loved the contrasting materials — the calf hair felt warm for cold weather and the textural shaft was insulting and soft. But for a classic riding boot that can transition through more than just fall and winter, I think I would have opted for the brand’s standard black leather finish.

From ballet flats to sandals and loafers, Madewell’s reasonably priced, all-leather shoes regularly get written up around here. The leather quality was the first thing I noticed about these, plus the very classic silhouette, which included a straight shaft and rounded toe. While the sole felt plenty cushy, the upper part of the boot was a different story; I have narrower feet, and the heel and mid-foot still felt snug. I imagine the leather will stretch out as I continue to break them in, but for those reasons, I decided to keep looking.

The Bridget boots from Sézane have a roughly 1.6-inch heel, but they still felt very flat in a good way: The insole is cushioned with nice arch support. The glossy finish made them feel more fashion-y and less traditionally equestrian (which I associate more with a light shine or matte leather). The wider shaft fell further from my calves, creating a more versatile silhouette that could be worn with shorts or with straight-leg jeans tucked in. I went with my normal women’s size 9 (the product description says the brand has updated its U.S. size grid) and it did feel like there was some sliding in the ankle or heel area, but wearing thicker socks seemed to help. Unfortunately, these don’t come in half-sizes, and if you are between two shoe sizes, Sézane says to choose the size above.

I didn’t realize how heavy the other riding boots I’d tried were until I put on the Dolce Vita Tywin. These knee-highs are sleek and lightweight, which made me feel like I was ready to saddle my imaginary mare and zip around a ring. They are rather minimalist and stripped down in design compared to other styles on this list. What sets them apart is the one-inch block heel, plus an outsole made of a lightweight recycled synthetic, rather than a heavy rubber or thick stacked wood. My only concern is that over time, the simple sole could flare up my tender plantar fascia — but during my initial wear testing, I didn’t notice any foot pain.

I’ve owned Frye’s signature Campus boots for about a year now, and they get better with every wear: more patinated, more formed to my foot, and more reason for why the style is much loved. Still, the $500 price tag is steep, so I decided to try the Quinn style, which is under $330 and has full-grain leather. I’m always in the mood for some gold hardware, and these have brassy D-rings and side zippers. The heel looks pretty minimal at first glance, but it’s actually about 1.4 inches thanks to a hidden internal wedge; I could immediately feel the slight lift. The shaft, or collar, is cut to be higher on the outside and lower on the inside, which is actually typical in real riding boots for outer protection and to prevent pinching inside the knee.

These nearly made the top spot, but the two-tone black-and-mahogany leather definitely makes these a more unexpected equestrian boot than one in a solid leather color. If that’s what you’re going for, the Quinn fits the bill — I know I’m still going to wear mine a ton this fall, but they may take more proper styling. For a more classic Frye riding boot, I’d opt for the Phoebe below.

In addition to suggesting the Quinn, Frye’s brand representative recommended I try the new pull-on Phoebe boots. These aren’t as glossy as the Sézane pair, but the soft leather and its pebblelike surface reads somewhere between lightly shiny and matte depending on the light. These have a curved shape at the top with the shaft rising higher on either side of the knee. I found the design gave room for my kneecap and really lengthened my leg. They have some western flair, which reminded me of my Staud Western Wally pair. Compared to the Quinn boot, which has a prominent D-ring, the only hardware on the Phoebe is two small buttons that sit on either side of the outer pull tabs. The sole felt super comfortable from the moment I first tried the Phoebe, and the outsole is made of lightweight EVA with a textured tread ideal for slick surfaces. There also seemed to be more wiggle room in the toe box and heel-cup area, but nothing that felt unstable or like my feet were sliding around.

I don’t know why I’m surprised that Lands’ End makes well-made boots. It’s been almost exactly two years since freelance contributor Erika Veurink wrote about how the brand’s solid quality and ability to ignore fast-moving trends means it flies under the radar and feels versatile and truly effortless. These boots are no exception. Made from smooth, matte leather, they have full-length interior zippers and a handy elastic that runs down the back shaft for extra stretch but is hardly noticeable. The low 1.25-inch heel combined with an EVA foam insole is incredibly comfortable. The outsole is rubber, which feels plenty durable for days when sidewalks are covered in salt and sleet. I guess my only complaint would be the silver hardware on the black leather (the brown rich-coffee leather has gold hardware). That said, I decided the hardware color shouldn’t be a deal-breaker when the boots are as comfortable as they are and come with an under $300 price tag (even less when they’re on sale).