What I Take Long Walks In
With the exception of running shoes, the most comfortable shoes I’ve worn have always been built on Plantation crepe. Crepe refers to a sort of soft rubber - usually slightly yellow-ish in color - that comes in large sheets. Shoe manufacturers take these sheets, cut them down to the size and shape necessary, and then layer them to form a sole. The result is something that’s very, very comfortable. They make you feel like you’re walking on soft clouds, or more realistically, like those big rubber pads that toddlers play on. 
The upside to crepe is that they’re comfortable, particularly on hard concrete, and look suitably stylish for spring through fall wear. The downside is that they might not last as long as a pair of hard-bottom leather soles. Still, they can still be replaced by an experienced cobbler when the time comes. I’ve also read that crepe can get rigid and crack. I don’t know if this is because of harsh weather conditions or just plain age, but for what it’s worth, that’s never happened to any of my crepe soled shoes. 
There are a number of shoe styles that are commonly made with Plantation crepe - boots, plain toe derbys, moccasins, etc. My favorites are perhaps brown suede chukkas, which I think look particularly nice with cotton trousers, casual shirts, and even the occasional soft-shouldered odd jacket. The pairing of suede and crepe makes for a particularly stylish casual combination, and you can find suede, crepe soled chukkas at a pretty wide range of price points. On the high end, A Suitable Wardrobe has my favorites - a really handsome model that looks sleek enough to be worn with grey wool trousers. For something more casual and affordable, consider Church’s Sahara, Loake’s Gobi, or Clarks’ desert boots. The third retails for about $120, but it’s not hard to find them for under $100. Just Google around or check eBay. 

What I Take Long Walks In

With the exception of running shoes, the most comfortable shoes I’ve worn have always been built on Plantation crepe. Crepe refers to a sort of soft rubber - usually slightly yellow-ish in color - that comes in large sheets. Shoe manufacturers take these sheets, cut them down to the size and shape necessary, and then layer them to form a sole. The result is something that’s very, very comfortable. They make you feel like you’re walking on soft clouds, or more realistically, like those big rubber pads that toddlers play on. 

The upside to crepe is that they’re comfortable, particularly on hard concrete, and look suitably stylish for spring through fall wear. The downside is that they might not last as long as a pair of hard-bottom leather soles. Still, they can still be replaced by an experienced cobbler when the time comes. I’ve also read that crepe can get rigid and crack. I don’t know if this is because of harsh weather conditions or just plain age, but for what it’s worth, that’s never happened to any of my crepe soled shoes. 

There are a number of shoe styles that are commonly made with Plantation crepe - boots, plain toe derbys, moccasins, etc. My favorites are perhaps brown suede chukkas, which I think look particularly nice with cotton trousers, casual shirts, and even the occasional soft-shouldered odd jacket. The pairing of suede and crepe makes for a particularly stylish casual combination, and you can find suede, crepe soled chukkas at a pretty wide range of price points. On the high end, A Suitable Wardrobe has my favorites - a really handsome model that looks sleek enough to be worn with grey wool trousers. For something more casual and affordable, consider Church’s Sahara, Loake’s Gobi, or Clarks’ desert boots. The third retails for about $120, but it’s not hard to find them for under $100. Just Google around or check eBay.