What is the most comfortable shoe possible? Chukka boot in chromexcel?

I've never owned a pair of chukka boots, nor have I ever owned anything in chromexcel. But from what I've read about both, combining the two should make for one incredibly comfortable shoe.

A chukka boot that secures at the ankle, allowing the foot to move comfortably within the shoe, make out of a soft pliable durable oily leather. Or would cordovan beat out chromexcel here in the long run after break in?

Anyone have any other ideas on super comfortable shoe and leather combinations?

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The most comfortable shoe is the one that fits you best. If your foot is moving freely within the shoe, it does not fit. To the extent that the material choice of the upper impacts comfort, I'd put suede ahead of CXL and everything ahead of shell. But the impact on comfort is minimal relative to the question of fit.

Nike > Adidas.

CXL is nice for the way it stretches and conforms to your foot (and ankle), especially for the weight/thickness. However, it can stretch too much in some circumstances. I've never experienced the same with cordovan. I personally haven't found a chukka that fits and gives the support I need due to the few highly placed eyelets on most I've tried- and I've tried a few. Another comfort aspect is the type and composition of the sole. I've had super soft leather boots that fit well but the sole was too stiff and didn't flex with my foot.

The most comfortable shoes I own are double-soled longwing bluchers in thick leather. They fit exceptionally well. If they were even a tiny bit off, they'd be intensely painful because they're so rigid. Because they fit well, they're incredibly supportive.

That said, there are Clark's desert boots in CXL-ish leather on crepe soles. I've only had suede desert boots (and not from Clark's), but they're as comfortable as a slightly-loose shoe can be.

I admit I don't fully understand the concept of Chukka. I tried one on in a department store - some no name brand - and it felt incredibly comfortable. My feel did not feel constrained, and yet the shoes felt secure. Then again, all I did was walk back and forth across carpet, so I'm not sure how it would feel walking long distances.

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I end up walking long distances in my suede C&J Chukkas and they are fine. That said the fact that they don't attach as well as a normal boot (2 vs. what 8-10 pairs of lace eyelets) makes them less comfortable to me. I find a real full boot, regardless of material, that I can lace tight enough to have it move with my foot to be much more comfortable.

Though really my beat to crap New Balance runners that I slip on like loafers probably destroy all my nice shoes in the comfort department.

At first I thought the question did not make sense. As RogerP pointed out, the most comfortable shoe is the one that fits you best. If a shoe really fits, it doesn't matter if it's an oxford, a blucher or a Chelsea boot.

If you mean 'most forgiving' or 'safest', especially when you buy something on the Internet, that's a different story and your choice actually makes a lot of sense, except that suede might still be better. If you buy without trying on, I'd be cautious about oxfords and double monks, very cautious about Chelsea boots and would ignore loafers altogether. So, yes, boots (any kind of boots except for balmoral) in suede might do the trick. In fact, you can just err on the larger side and, if necessary, adjust the volume with sock thickness. But 'safest' is not the same thing as most comfortable.

good stuff