Shopping for a pair of tall leather riding boots is exciting, but it can be daunting too. It’s rare that we spend a large chunk of our hard-earned cash on boots – the right pair can last for years, so we want to make sure we get it right.

If you’re buying your first pair of English style boots, or if you’re replacing a pair of old faithfuls, don’t go for luck over judgment. Follow these tips and you’ll soon be doing your horse proud and wowing the judges in the perfect pair of boots.

Features To Look Out For:

Field Boots or Dressage Boots?

Dressage boots are often made of much stiffer leather than field boots. Because of this, they won’t ‘drop’ with wear as far as a field boot will. The ‘tube’ of the boot is also cut straighter – it’s wider in the ankle area to allow the boots to fit over the foot.

Field boots have lacing around the ankles which can be tightened once the boots are on to allow for a more fitted look. The softer leather will wrinkle and drop with wear, making the boots appear shorter.

If you are going to wear your boots in the show ring, check which boots are most appropriate for your discipline.


Zippers are now common, even in dressage boots. They can help achieve a better fit around the calf and make boots easier to get on and off. But, zippers can have a downside.

High-quality boots can outlive their zippers. It is possible to have them replaced, but you may not want the hassle.

Zippers need a bit of TLC from time to time. If they aren’t kept clean they can break and they can break if you step on the open zipper as you put your boot on. A little care will go a long way to keeping your boots in top condition.

If you look for a boot with a quality zipper, you’ll enjoy the advantages for many years though.


Elastic panels alongside the zippers on boots can be very useful. They allow boots to fit better around the calf and increase comfort while riding.

Another plus point is that the elastic will adapt to your winter and summer riding gear.  There’s no need to go without those warm, fluffy socks in cold weather.

Spanish Cut

Many boots are cut higher on the outside of the knee. Known as ‘Spanish Cut’, this makes the boots look longer and more flattering.

Spanish Cut boots will still look long enough even after the boot has softened and dropped with wear and when you lower your heel to ride.

Soles and Heels

Some boots look like riding boots but they’re really intended for walking around the barn and working. They will have a ridged sole and might not have a separate heel. While grippy soles are great on the ground, they’re not suitable for the saddle.

For riding, you’ll need a smooth sole that will slip in and out of the stirrup easily. A low heel is also important to stop your foot slipping too far forward and getting caught in the stirrup.


How To Measure For Boots

Measuring your leg before you start trying on boots means you’ll have an idea which pair to start with. The knowledgeable folks at Ariat recommend the following method to focus in on your perfect fit.

To measure correctly, take off your shoes and sit down with your feet flat on the floor. Your knees should be bent at 90°. Measure around the widest part of your calf making sure you keep the tape level for an accurate measurement.

Next, measure from the floor at your heel straight up to the bend at the back of your knee. Add 1” to this measurement.

Now you can take a quick look at the labels to see which boots are a likely match and avoid the ones that just won’t work for you.

Foot Fit

Riding boots are designed to be narrow in the foot so they can slip in and out of the stirrups easily. Sometimes this can be a bit of a shock to feet that are used to more casual footwear but remember that you won’t be walking far in these. On the flip side, you don’t want boots that are so tight they hurt.

Check that your toes aren’t touching the end of the boots and that your heel sits comfortably in the heel cup at the back. When you walk, your heel shouldn’t move up and down inside the boot.

If you do find a pair of boots that fit really well overall, but you are concerned about tightness across the widest part of your foot, there may be a solution. You could try some boot stretch spray or boot stretchers to ease that area.

Calf Fit

It helps to make your leg look extra long and elegant on horseback if the calf width of the boot is as narrow as possible compared to the length. While we’re sure you’d love to look elegant, it’s also important to keep your circulation going. There will be a boot for you that has a balance of elegance and functionality.

If the boot you are trying on has a zipper, it’s okay if closing that zipper is a little difficult at this stage. Once the leather gives you should end up with the right fit. An easy to pull zipper now might mean a floppy, inelegant fit later.

Boots that are too loose around the calf can also make it difficult for you to get your leg in the right position when you ride – not good in the ring.

Boot Height

The height of your boots won’t just affect how good they look – it could affect your riding too. If boots are too short they can catch on the saddle flap, and if they’re too long they may make it difficult to get your lower leg into position.

The main thing to remember is that leather boots will drop about 1” or 2”  with wear. How much they’ll drop exactly will depend on how stiff the boot leather is to start with.

When you try on a boot and bend your knee, there should be a slight wrinkle in the leather towards the back of the knee. As the ankle area of the boot wears in, the leather will settle and the top of the boot will drop, eliminating this wrinkle.

With your knee bent, the front of the boot should sit just under the kneecap.

Many new boots can dig into the back of your knee at first. It can help to place heel wedges inside for the first few weeks. These lift your heel a bit, taking the pressure off the back of your knee. They also make the calf slimmer, so there isn’t as much pressure in the calf area. You can remove heel wedges once the leather has started to give.

Trying On Tips

  • You’ll probably feel a bit silly, but squat in a jumping position to get an idea of how the boots will feel around your knee and ankle when you’re in the saddle.
  • Take a friend with you – they’ll be able to give you a second opinion and help you tug those tight boots off!
  • Don’t forget that leather boots will give and drop, so a little discomfort because of the height is what you want at this stage.
  • Wear the same type of socks and trousers to try on as you’ll be wearing under the boots when you ride.
  • ‘Swagger Tabs’ (the leather straps on the top side of boots, often with a decorative stud) are just for show. They aren’t strong enough to help pull a boot on. Because of this many manufacturers are now stitching them down all the way around to stop people getting their fingers underneath.
  • It can take between 1 and 6 weeks to break in your new boots fully, depending on stiffness.

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