I've tried many chukkas and ankle boot models but this is the best. The leather is substantial but pliable; it is getting softer with every use but continues to look smooth.
The construction fits my narrow heel and wide forefoot very well - no slipping, no sliding, no pinch-points. I've worn the shoes with my insert orthotics for day-long walks in complete comfort but I wear them without orthotics also - the built-in support is good enough for casual wear.
I especially like the low, "natural" heel and the cushioning effect of the sole.
The fact that the soles are not "crepe" soles was very important for me because, no matter how carefully I walk, I end up sliding on wet pavement with crepe soles.
Style was not an issue for me but, surprisingly, I've been getting flattering remarks when I wear the shoes; I suppose the current "trend" is moving back to more rugged-looking shoes.
Whatever the style trend is, these are great shoes that I know will serve me well for a long time!