The Best Classic Riding Boots to Wear All Winter Long

Simple, affordable and classic!

These Sam Edelman boots are tall, pull-on style boots with a round toe. They’re made from 100% leather and hit about knee-high.

Also available in wide calf options!

Don’t sleep on Madewell’s shoes.

They have a great range of tall riding-style boots. These are made from pigskin, with a round toe and slight stacked heel.

Super comfortable and well made, supple leather.

If you want the look of a classic riding boot but are worried about comfort, try these Dr. Scholl’s boots.

They’re knee-high riding boots with a cushioned foam footbed and very low stacked heel, making them easy to walk in. 

Made from a breathable PU and lined in cloth, they’re also easy to get on thanks to a side zip.

These tall riding boots combine a distinctly equestrian vibe with a modern silhouette.

The boots have a low 1″ heel, memory foam cushioning for comfort and slight almond shaped toe.

Larroude is a Latinx owned brand, started by the former fashion director of Barney’s. All of the brand’s shoes and bags are made with high quality leather from Brazilian tanneries.

I’m a big fan of German shoe brand Aeyde.

All of their shoes are well made from high quality, super soft leather and incredibly comfortable to walk in all day long.

I have a pair of their classic mary janes and am eyeing these tall riding boots next!

They come in lots of different colors and feature a classic riding boot silhouette with a modern slightly chunky sole.

These classic riding boots from Cole Haan combine style with function.

They have a low block heel, handy ankle zip and pull-on tabs so they’re easy to get on and off.

Best of all, they’re waterproof!

These are great riding boots to wear all winter long if you live somewhere cold, snowy or rainy.

These Jack Roger’s riding boots are classic… with a twist!

They have a whipstitch detail at the cuffs that elevate these tall boots into something unique.

Available in 3 colors, they’re made from 100% leather, come with a cushioned insole and have a statement almond toe.

A zip closure makes them easy to get on and off!

I saw these Jil Sander boots and immediately fell in love.

They have an extra tall boot shaft and asymmetric cuffs for a little something different.

I like the flat sole and minimal heel, which keeps them flat and easy to wear all day long.

They’re a little pricey but I haven’t found any other riding boot that compares! Made in Italy from 100% buttery soft calfskin leather.

Loeffler Randall’s tall boots are the perfect combination of a riding boot and combat boot.

They have a durable smooth leather upper and a chunky, stacked sole. Inside, the footbed is padded so you have all day cushion and comfort.

The chunky block heel keeps these a bit more interesting than your average riding boot!

2 inch heel height

Anine Bing’s riding boots are the kind of tall boot that will match any outfit.

They’re made from smooth cowhide, have a pointed toe and slightly glossy, sleek finish. These are a simple pull-on style, with a slim shaft and flat heel.

Want a riding boot that has just a hint of western flair?

Then check out these boots from LifeStride!

They have a slight stacked heel and almond shaped toe. Inside, there’s tons of cushion, support and flexibility so you can comfortably wear these riding boots all day long.

Camper is a family-owned brand based out of Mallorca, Spain.

They make classic shoes with a twist and their black riding boots are no exception!

These leather boots are made from 30% sustainably sourced materials. 

They have a flared block heel, streamlined shaft and durable rubber sole. If you’re looking for classic riding boots with a slightly playful silhouette, you’ll love these!