I've only been wearing them for about a week now, but so far these shoes are incredibly comfortable. I work in an environment that require business casual dress, which usually means some type of loafer or oxford. Since I've had these though, I've been creating outfits around them just so I can wear them to work every day. They're that comfortable! We've also been experiencing some abnormally heavy rain here in TN this winter, and despite purposely testing these shoes in deep puddles, my feet have remained dry. I can't speak for the long term, but so far these shoes are great. Sizing seems accurate as well.