I was recently asked which shoes I preferred for a guy: black top-siders with red stitching, or the more classic navy with white accents. The concern was that the black pair, even though they had fabulously unusual contrast stitching, would be too obvious. Trying too hard. Possibly douchebag territory. I say it depends on the rest of the outfit. Wearing top-siders in general already says something. Day-to-day, if you aren't going to put forth the effort and want something to throw on without thinking, I'm going navy with white, especially once they're broken in. I see the black ones on someone who already looks like he kind of tries, so this extra step isn't much. You're already a little self-conscious, which is fine, because you look good with your tight black jeans and straw fedora. You could also go super-preppy for the rest of the outfit, then bust out with these. (sidenote: I like the slouchiness of the black pebbled leather. Why don't the navy come in pebbled?)
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