Are Riding Boots Still in Style in 2024? + 6 Suggestions

Woman Wearing Riding Boots

If there is one thing to love about winter, it’s most definitely boots. Especially high boots that keep you warm and cozy, even more so stylish and chic ones.

A boot style that has been around for decades is the riding boot, initially designed for horse riders.

They are called riding boots because of some design specifics, such as length, heel, toe, and outer sole, which set them apart from other boot styles.

Today we will be dwelling into different aspects of wearing riding boots, styling them, and answering a very important question: Are riding boots still in style?


You might also like: 8 Best Riding Boots For Women To Try This Year

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Are Riding Boots Still in Style in 2024?

Well, it depends on what look you are going for. If you prefer the vintage style of clothing, then absolutely! Think Nancy Drew and you’re in the right direction.

But if you are thinking that your rocker style, black leather jacket, and rugged jeans would go well with this type of boot, we’d recommend otherwise.

Riding boots are casual, yes, but they are also quite elegant, that’s why they should be styled accordingly.

With some finesse and a few accessories, riding boots are one of the easiest and most practical boot styles to wear in winter.

What Classifies As a Riding Boot?

horse riding boots

In the old days, riding boots needed to be knee-high, at least, have a low heel and sturdy toe to keep the rider’s feet and legs protected from the saddle and to prevent sliding of the foot through the stirrup.

The outer sole was also very lightly textured, if at all, so in case the riders fell off the horse, the boot would not get caught in the stirrup and endanger their life.

Nowadays, however, trendy riding boots that are intended for everyday wear come with textured and even ridged outer soles, a variety of toe types, and heels that go up to 2-2.5 inches.

The outer sole texture prevents slipping on wet or frozen ground, whereas the toe and heel are more of a fashion choice.

One thing that hasn’t changed, though, is the high shaft.

How To Style Riding Boots?

Boots in general are quite easy to include in different outfits as there are numerous designs, heights, and colors that make all of this a simple process.

Riding boots are quite casual in style, so they go very well with an overall casual outfit.

To give you a better idea, here is a short guide on how to and how not to style riding boots:


When it comes to wearing pants and boots together, the question is whether you want the boot to show or not.

  • If not: Wear wide or suit-style pants that go over the boot, covering it.
  • If yes: Jeans. Honestly, if there is one type of pant that goes with any shoe it’s jeans. You can easily slide them into the shaft of the boot and be out the door in a breeze.


If you are planning on combining these two, opt for casual, flowy dresses, preferably short ones, so the boot shows.

Avoid dresses that are more suitable for a night out as they would look better with high heels.


Knee-length skirts look great with riding boots. Especially those in a vintage style as they match the casual and old-fashioned look of the riding boot perfectly. Especially with a blazer on!

You might also like: The Best Flattering Skirts for Big Hips and Thighs


You can wear anything, any style, it’s your body at the end of the day. But if there is one thing you’ll take from this article, do not wear riding boots, or any high boot for that matter, with cropped pants. Just don’t!

We are finally at everyone’s favorite part, the actual selection so let’s get started right away.

6 Riding Boots Suggestions

Dream Pairs Knee High Riding Boots

Dream Pairs Knee High Riding Boots
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The first pair of boots is by Dream Pairs, the Utah Knee-high riding boots design.

They are made of leatherette upper, while on the inside are lined with faux fur. This creates the perfect boot for rainy and cold days, as the outer part is water-resistant, while the inner lining helps insulate and keep your feet and legs warm.

The style is very elegant, with various stitching details and stud buttons on the outer side.

The outsole is made of TPR, which provides cushioning by being soft yet sturdy. A flimsy outsole in heeled boots and shoes is not only uncomfortable, but it would also lead to damaged feet. Luckily you won’t have to worry about that with the Utah boots.

Great also for wide feet because of the rounded toe and suitable for women with wide calves, as it stretches in the back. Along with that, there is also a buckled strap for adjustment.

They measure approximately 17.5″ (44.45 cm) tall and come in 14 colors, such as Camel, Khaki, Brown, Black, and Grey.

You might also like: 8 Over-The-Knee Boots to Try in Winter + Some Tips

Frye Melissa Tall Riding Boot

Frye Melissa Tall Riding Boot
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Stylish and quite authentic in design, Melissa by Frye is both comfortable and high quality. Frye is the oldest shoe-making company in the US and they have managed to bring out the classic riding boot look perfectly in this design.

Made of genuine Leather both inside and out, these boots are weatherproof and easily adaptable to different foot shapes.

The shaft measures around 15″ (38 cm) and comes with a deep back notch, a famous and specific detail of riding boots. And if you are an actual horse rider, then these boots will be right up your alley.

The rubber outer sole, along with the arched foot of the boot make for a great combination for comfort when walking.

They open on the side with a half-zipper and are very easy to put on, as you can pull them up with the side loops on the opening. The stitching details add to the design of this boot and the color selection includes 4 options: Redwood, Black, Burnt red, and Camel.

Sam Edelman Penny Equestrian Boot

Sam Edelman Penny Equestrian Boot
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Also a boot made of real leather, the Penny Equestrian boot design by Sam Edelman comes in a bold and fashionable look.

With an angled opening that measures 14″ (35.5 cm) around, it is designed to fit wider legs also. The asymmetrical opening comes with a single-side ear pull, which will help you put the boots on.

However, no worries as the zipper on the back is full-length, this way the boot opens completely. There is also a snap tab on the zipper to prevent it from accidentally opening.

The outer sole is made of rubber and it is quite arched, helping relieve pressure off the feet and providing cushioning. It is also designed to grip well when walking, so you won’t have to worry about slipping.

The shaft measures 15″ (38 cm) from the arch and it comes with a 1.25″ (3 cm) heel. There are two color options to choose from: Black leather and Whiskey leather.

Naturalizer Dev Riding Boot

Naturalizer Dev Riding Boot
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For those among you who prefer a higher heel in your boots, Dev by Naturalizer is a beautiful design that goes well with jeans pants, skirts, and dresses.

Decorated with straps and buckles around the ankle and with a heel that measures around 2″ (5 cm), these elegant boots are a must-have for any style.

They are made of real leather inside and out and come with an elasticized notch on the back, for a better fit. There is a single loop pull on the side of the opening and a full-length main zipper on the inner side.

These boots are waterproof and come with a 15″ (38 cm) shaft. The synthetic outer sole is thin, anti-slip, and comfortable to walk in.

This design has a rounded toe and because they are made of leather, they adjust to different foot shapes over time. The color selection includes five options: Saddle, Grey, Black, Oatmeal leather, and Oatmeal.

Easy Spirit Jimlet Riding Boot

Easy Spirit Jimlet Riding Boot
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Sleek and feminine, the Jimlet Riding Boot by Easy Spirit is a design that you cannot overlook. Very casual in style, this boot is a great day-to-day shoe for women who are a lot on their feet.

With a cushioning, flexible rubber outer sole, and made out of leather, you will be comfortable and won’t have to deal with any blisters or foot pain.

The outer sole is also designed to be anti-slipping so you can wear them any day. The shaft measures 15.5″ (39 cm) tall and the opening is 16″ (40.6 cm) around.

They come with a low heel and closed deep botch on the back. As a detail piece, but also used for adjustment, there is a buckle and strap all around the top back of the boot.

This design comes with a full-length zipper and is available in the colors: Black, Brown, and Dark brown.

Tommy Hilfiger Madelen Equestrian Boot

Tommy Hilfiger Madelen Equestrian Boot
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Last but not least, it’s the Madelen Equestrian Boot by the popular brand Tommy Hilfiger. This is a very interesting design that resembles old-style riding boots, with its arched foot and wide heel.

The outer material is a combination of PU leather on the foot and top, and textile in-between. This makes it resistant to water, durable, soft, and flexible on the leg, for a more comfortable wear.

The top measures 14.25″ (36 cm), but it is also partly elasticized so it can be worn by women with a wide calf, too. Onto the foot, as we mentioned, it is arched and comes with a narrow rounded toe, so it isn’t too suitable for those of you who have wider feet.

The outer sole is rubber and quite sturdy, and because of the narrow arch, the heel goes out on the sides a bit, creating an asymmetrical look that goes great with the angled top.

The shaft measures around 15″ (38 cm) and there are three colors to choose from: Grey flannel / Brown, Black, and Medium blue.

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