Have you sole pictures?
On the front hooves the heels are starting to collapse as can be seen by the curve in the event lines towards the heel, seen best on the front foot with the black spot.
Are you asking for any particular reason?
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Can you take some pictures of the fronts from exactly side on, with the camera down almost on the floor. It's difficult to see the angles of the feet from the shots you've posted.
Your farrier is shoeing to bring the toe right back which should help with the tripping. How long has he been shoeing him for you?
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The heels are contracted which is not really what you want. However he’s not overly long at the toe which is good.
You see, I think he is, but the farrier is doing a great job removing it and bringing the breakover back, but we need the pix from the floor to check.
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If he was mine, I would be tempted to have the shoes removed on the 31st Aug. I would make sure that they weren't trimmed in any way, just shoes off.
Then I would start to walk out in-hand on tarmac to see how he's doing. Is he comfortable? Are there any spots where gravel driveways have deposited gravel on top of the tarmac (I'd be back with a broom to sweep it)? Is he landing toe first, flat or heel first?
If I then thought, OK he's comfortable on the roads, I would then ride but would build up the distances slowly. This gives the hooves a chance to respond to the new wear level. They will grow more if they need to but it doesn't happen immediately. Then you get to the point where you ride the bleddy thing for hours and hours, you're trotting, cantering, going up and down massive hills and it still needs trimming! Can you tell that I never achieved the holy grail that is the 'self trimming' horse?