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Every once in a while, we run across an item that’s impressive simply by virtue of being so difficult to wear.

For instance, how does one approach this Band of Outsiders button-up?

Is it too busy to be paired with jeans and left untucked? Maybe under a gray blazer that’s rumpled enough to seem casual? It’s going to take a lot of careful consideration before pulling this one off.

But we’ve never run from a challenge before…

—R.B.

CONTRIBUTORS

  • Russell Brandom