If you're going for a simple leather shoe, don't forget the simple part. This derby from Church's is crafted from a single piece of leather that has no marks or flaws, no toe caps or stitching. All polished, streamlined, simplicity.
The upside of the whole upscale-sneaker trend of the past few years is that it's become easy to get a sneaker that's both really well made and really comfortable. This turquoise calfskin low-top by Bally, which has been making luxury footwear for 160-some-odd years, will mold to your feet and look good with pretty much everything you own. We wouldn't work out in it, but there's no good reason we couldn't.