I bought these as my fashion starter kit. I try and stay away from baseball caps and athletic footwear. Not trying to look metrosexual either. Just trying to look like a dude that gives more than just a little about what he is trying to communicate to the ladies. Will go with most anything. Not really a shoe for support, but are comfortable like a loose fitting loafer. Instantly worn in. Leather is soft, and sole is some weird composite I see on shoes I call hushpuppies. Stop on a dime on carpet if that is your thing. First pair of "Chukka" style shoe. Like the cut. Many colors. Kind of like the chuck taylors of the middle class office crowd. This only led me to like shoes like Red Wing heritage collection. The addiction starts slowly, and then BAM, you are justifying $350 boots. But dam. You are starting to look like a player. No go out there and seduce.