Leather Chicago
What color and kind of socks should I wear with brown leather sneakers?
I just started dating a girl and I would like to impress her with my sense of style. I'm taking her into Chicago all day Saturday. I'll be wearing a brown and white shirt, khaki shorts and brown leather sneakers. White socks just don't look right. But you can't wear khaki or brown dress socks with sneakers. What is the correct choice?
if you're wearing khaki shorts i think you should wear heel socks. it never looks good (at least to me) when guys wear shorts with socks taller than their shoes. it just reminds me of how boys dressed in elementary school and trust me you don't want her to be thinking about that on your date 
Best of luck!
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