Best Riding Boots Guide: How To Wear Traditional Dressage & Field Boots

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Riding Boots: What They Are & Their Features

Riding boots, in the English tradition, are boots that are made specifically with horseback riding in mind. We will be focusing on classic knee-high boots in this article. If you’d like to read about jodhpur boots, click here to jump to that article. For now, here are some of the main points of what makes a riding boot a riding boot:

• Knee-high to protect against friction and pinching of the leg skin against the saddle.
• Traditionally a pull-on style with no laces, straps, or buckles.
• The leather of the sole is actually very flexible and smooth. This is to allow additional manoeuvrability in the stirrups and to prevent the rider from being caught in the stirrups in case he falls off.

Furthermore, there are arguably two distinctive types of traditional riding boot. The first, most common type is the dress boot, which is often worn for dressage and other formal eventing equestrian sports.

Meanwhile, the field boot is worn for outdoor equestrian activities such as hunting or hacking. However, cross-country riders will often favour Jodhpur boots with short chaps, which allows for greater flexibility.

You can easily spot the difference between dress and field boots by their appearance. While both are knee-high and usually black, field boots will have laces whereas dress boots are plain. This is because dress boots are considered to be more formal and field boots have a more rustic appearance.

Horseback History & The English Tradition

Humans have been riding horseback regularly since about 800 B.C., and the process has certainly been refined over the last 2800 years or so. Using horses as beasts of burden was one thing, but being able to ride them was a different story altogether. You could deliver messages faster and escape enemies easily if they were on foot. Groups with strong cavalries were formidable in warfare until the invention of motor vehicles, which rendered equestrian efforts on the battlefield obsolete.

Naturally, riding horseback provided challenges in terms of the comfort of the rider. In the way that form tends to meet function at some point or another, riding gear was invented to ease the burden on riders’ legs.

Before the invention of the jodhpur pant in 1890 ushered in widespread use of jodhpur boots as riding footwear, the riding boot was the option to wear while riding. They were largely replaced by the jodhpur boot for the same reason that most people do anything: it was easier.

Getting jodhpur boots on and off is no big deal, you just remove them like you would any other shoe. Taking full riding boots off, however, is a bit of a project. It requires either:

• A boot jack
• A staff of people to help you

Not many of us nowadays are so wealthy that we have a team of people to help us with our equestrian endeavors, and a boot jack is just another thing to have to worry about. It’s easy to see why folks went to using jodhpur boots so quickly.

Knee-high riding boots are nowadays typically reserved for formal occasions like hunting or eventing, whereas jodhpur boots are used more regularly in everyday hacking, cross-country, or dressage practice.

How To Wear Riding Boots

We admit that seeing riding boots on men in a non-riding context is rare. Peculiar, even. With that said, the English riding tradition has influenced a lot about menswear. We wouldn’t have center vents without horseback riding, nor would we have hacking jackets or slanted pockets on jackets (sometimes called “hacking” pockets, so named after the equestrian activity with which they’re associated).

With that said, Wellington boots (“wellies”) are based off of the riding boot design, and these have seen increased popularity among men in recent years.

Furthermore, Ralph Lauren’s Polo line is, literally by name, based off of the equestrian tradition.

The footwear deserves its due as well!

Formality

Riding boots don’t play by the same rules as normal footwear when it comes to formality. There is, however, a uniform worn along with them, which includes:

• Tan Jodhpur trousers.
• White button-down shirt and tie.
• Tweed or block-colour hacking jacket depending on the event.

The colour of your tie or jacket are usually dictated by both the sport and your position, affiliation, or rank in the event. However, we don’t advise wearing this outside of a riding context unless you’re involved in performance art or a practical joke of some kind.

Seasonality

One can theoretically ride in any season, though it’s customary to avoid the dead of winter and the hottest summer days for long periods of time. While horses are very resilient animals and require regular exercise, they shouldn’t be pushed too hard in adverse conditions.

Nevertheless, riding boots are perfectly wearable throughout the year. As traditional models are rarely insulated and quite thick, they can be uncomfortable during winter or summer. However, more contemporary styles have been designed with better ventilation and insulation to cater for these needs.

Should I Buy A Riding Boot?

We understand that it’s impolite to answer a question with another question, but we have to in this case:

Do you ride horses or plan to take up horseback riding in the English tradition?

If the answer is yes, go for it! Invest in a good pair so that they last! A pair with an angled shaft will reduce wear as it already accommodates the “toes to heaven, heels to hell” mantra.

The the answer is no, don’t buy these boots. It’s one thing to be a poser, but quite another to be a poser in super rare clothing.

What Next?

Now that you have learned about riding boots, check out some our related footwear guides for men:

• Jodhpur Boot Style Guide
• Chelsea Boot Shoe Guide
• Best Dress Shoes For Men
• Most Comfortable Shoes For Men
• Men’s Shoes Homepage