Cherry Sock, Do You Wear Socks With Hey Dude Shoes?. In terms of just fashion, wearing your Hey Dudes with or without socks is totally fine, and so it really does just come down to personal preference.People also askYou will see more English now.Do you have to wear socks with hey dudes?Are you supposed to wear socks with loafers?Why does everyone wear hey dude?Are hey dudes just slippers?Feedback Chicago Blackhawks Socks, Do You Wear Socks With Hey Dude Shoes?. Jul 6, 2021 — Well, the simple answer is that it won't matter if you wear socks with Hey dude shoes or not. So long as you take precautions to keep your feet . Chip And Dale Socks, The Best Hey Dude Shoes To Wear With And Without Socks. Socks are not permitted in Hey Dude shoes because they are designed with comfort in mind. Trousers come in two varieties: long and short. 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