re: At what age are you supposed to start tucking your shirt into your shorts?

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That photo is a bit misleading. The tucked look there is superior. Now if the other guy had better fitting shorts and polo it would be a wash.

Now I’m hating on the look. I do it from time to time, but it just isn’t me. I am more with the shorts being casual crowd.

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I don’t think it’s a big deal, but tucking in your shirt will make you look taller and more fit assuming you are in shape