Islander writes: "Can I wear a polo shirt with a suit or sport coat?" Answer: You sure can, but it has a high degree of difficulty. The most important factor in making this work is selecting a polo collar with enough structure and heft to stay in place, otherwise it is going to slip under your lapels and look a bit s**t. There's a fine line between sprezzatura and looking like you aren't even trying. Shown: polo collars wilting and disappearing under Jack Victor (left) and Isaia (right) sport coats from the awesome Sierra Trading Post.

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