Absolutely agree with NinaJD. Trimming could definitely be a big part of the issue. (although being a young TB it’s probably not all of the problem) Long toes are a no no front and back. He may need his front toes ‘rolled slightly to help him break over sooner so his front feet get out of the way of his hind easier. Not seeing him in person though these things are just theory and guessing. He may already be trimmed properly for his conformation.
We have a QH gelding that lives in bell boots – 2 pairs -1 med and 1 large at a time. He doesn’t overreach though – he steps down sideways on the side of his foot and pulls his shoes off when he’s playing – we’ve watched shoes fly through the air when he bucks…… 🙂 Being horses they’ll think of some way new to cause us headaches every day.