Originally Posted by laufer
Really even for the custom made riding boots?
You’re asking about the break in? If so, yes, although it varies a bit from one manufacturer to another of course. It's not a question of improper fit or poor leather quality if that's what you're thinking. The leather in a dress boot is quite stiff, for functional reasons (and aesthetic ones too, to some extent). In particular, it takes time to loosen up the ankle so it can flex properly. There's always been a demand for well-maintained used boots for this reason.
Used Konig with ankle break:
For comparison, you can see some new Konigs here, along with pictures of the “half chaps” I mentioned earlier:
(You can see in some of those photos the distinctly Spanish top found in dress boots intended for dressage, where the outside of the boot, visible to spectators, is taller than the inside which is not. See photos of the riders of Vienna’s Spanish Riding School for a uniquely extreme instance.)
Zippers are a fairly recent addition (last 20 years, perhaps), and only more recently have they been allowed in competitions. Getting dress or dressage boots on or, particularly, off used to be quite a challenge before then, especially if you didn’t have a helper.
While I’m providing links, here are some Cavallo paddock boots:
The true dress boot, especially the dressage boot, is a thing of beauty and great craftsmanship. It deserves to be seen with the breeches and jackets which evolved along with it. Otherwise it’s like wearing a tuxedo jacket with denim jeans.