Earlier this week, we spotted model, television personality, author and entrepreneur Chrissy Teigen, who is also the wife of singer-songwriter John Legend, battling with her new tall riding bootson social media. This got us thinking on how to break in new long leather riding boots, a problem that many people find themselves in when they’ve treated themselves to some swanky new horsey footwear. So here’s some top tips that might just help you out…
How to break in new riding boots
1. Wear them around the house.
2. Heat the leather up with a hairdryer, then stuff with newspaper or boot trees that widen.
3. Walk up and down the stairs multiple times.
4. If they are cutting you behind the knee and need to drop a bit, heel lifts are great for this, or you could make your own out of some gamgee.
5. Riding in them a few times a week can help soften them and gives you a chance to get used to them.
6. If they are tight to pull on, try wearing tights or pop socks as they are made from slippery fabric, which could make life easier for pulling them on and off.
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6. Stand on the edge of a step or the bottom of the stairs, facing up, and drop your heels over the edge of a step. This will begin breaking in the boots at the ankle.
7. Be very generous with the application of leather conditioner, whether it is on the ankle area or at the top behind your knee.
8. Place boot trees in your boots whenever you are not wearing them to help retain their shape.
9. Apply a boot stretch spray to the ankles of your boots
10. Try riding a bike in your new boots.
11. If you’re suffering from blisters, or want to help prevent them occurring in the first plane, wrap your legs in elastic bandage such as Vet Wrap.
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Former web features editor, point-to-point editor and digital racing editor
Gemma is an experienced journalist, who was a member of H&H staff from 2014 to September 2025. She is passionate about all equestrian sports, including racing and point-to-pointing. She has enjoyed riding out for top trainers Nicky Henderson and Charlie Appleby and took part in a charity Flat race at Epsom in August 2018. Gemma’s has reported from numerous five-star events around Britain and Europe, as well as European championships.
