Q: Is it ever acceptable to wear a button up shirt untucked? I always tuck my shirts in, but my friend always tries to get me to untuck them. Should I ever listen to him on the topic of shirts (or anything else)?
A: We have discussed this issue before in a post entitled, "The Tyranny of the Untucked Sport Shirt." Unless the shirt is designed to be untucked, like this "Brando Military Shirt" from Edun, your shirt should be tucked in. In other words, ignore your friend in all matters, not just sartorial.