Q: I agree with your posts regarding the sport-shirts-untucked-from-pants plight. To push the point, however, what about shorts? I tend to tuck the shirt, yet sometimes I'm tempted to untuck it. I'm almost sure you'll say no good, but is this at least less bad?
A: Your instincts are on point, Chris. We are not fans of dress shorts, shorts with ties and wingtips, or any other look that might have people wondering if your work pants got amputated at the dry cleaners. For us, shorts are emphatically casual, so you'd think we'd be more open to untucking. And we are, sort of. With shorts, we like the partial tuck, which is to say, artful dishevelment.
How do you make it work? First, make sure that your shirt, be it a polo or a woven, is cut appropriately. If the fabric that falls beneath your belt-line is abundant enough to make a placemat, it's cut too long! If there's barely enough fabric showing to make, say, a bandana, then it's cut right.
Now that you're wearing the right shirt, tuck it in entirely, and pretend like you're a hailing a cab on a busy Manhattan street. Extend your arm, wave vigorously and impatiently. If you do this right, this should dislodge your shirt just enough to give the desired effect. And you're ready to go.
Earlier: The Tyranny of the Untucked Sport Shirt