ANSWERS: 3
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There are no longer any boundries in the world of fashion... but I wouldn't do it.
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It used to be fashionable to wear it that way, but I do not think so for now. It all depends on how to put together the style including your dress pants and shoes. I would rather wear it tucked in and choose less casual pants and shoes to bring out its relax style.
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If your shirt is tailored at the bottom you must wear it tucked in, if it's box cut then out is okay, but with a jacket over it this could make you look shapeless, and / or ruin the proportions of the cut of your jacket.
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