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Find a brand that feels comfortable and milk it. A few expensive comfortable pair will do it, rather than lots of cheap ones. Go a bit lower in the heel for comfort. Wear them while you can. Same with sandals.
I have these donald pliner shoes that I can wear all day. I don't wear them walking blocks on the sidewalk because I'd grind them down but I wear them in the house, car, errands inside stores... I think they're just beautifully engineered.
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I'm with Anne, but realize that was not your question.
If you can describe what is the biggest comfort issue, we all know a lot of shoe hacks/products/etc. that we can share. (Like, are the high heels rubbing somewhere? Is the ball of your foot in pain? Are your toes crunching up?)
For heels, I usually size up half a size, and pad the insides of the shoes with gel inserts and toe pouches. I trim the pouches if needed, so they don't show when the shoe is on my foot.
Also, if I know I'm going to be wearing heels for an extended period, I warm up my feet and legs - point and flex my feet, foot rolls, gentle stretching, and calf stretches.
