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Q&A:
Which shirts can be worn untucked and which should always be worn in?
All shirts classified as dress shirts should always be tucked in. Typically, a dress shirt will be more structured and crafted using finer cottons for sheen and softness. A simple indicator of a “dress shirt” is the sizing style--dress shirts will always be sized with a number indicating neck size and sleeve length, which provides a more customized fit that requires tucking. When it comes to sport, or casual, shirts a general rule to follow is this: always tuck in shirts with a rounded bottom hem; shirts with a flat, or square bottom hem (like polos) give you the option of wearing them tucked or untucked.
Read more at RL Style Guide