ONE award fashion does not give out is the “A” for effort. No matter how many hundreds of dollars and careful man-hours you spend on a look, it has to appear as if you got dressed while tranked on Haldol (or at least a Pabst Blue Ribbon or two), or you are likely to receive fashion’s cruelest judgment: “Trying too hard.”

So men who want to indulge in the latest trend  seen on fall runways from Giorgio Armani to Gilded Age, and on stylish guys all over town  should tread carefully. Wearing your pants nonchalantly tucked into your boots requires not only fastidious attention to detail, but also the right boots and pants.

“It’s definitely a good look,” said Madeline Weeks, the fashion director of GQ. “But the proportion of the boot and the pants has to be right. You don’t want to the boots to be too short or too tall  say, four to six inches above the ankle, or up to eight if you’re really going to go there.”

Boots that are too short, or knee high, can be too costumey. As can anything too slick, given that the aim is to suggest a woodsy outdoorsman style. You can’t go wrong with tried-and-true workingman classics from Red Wing, Carolina and L. L. Bean. Ms. Weeks also ticked off several fashion labels  Neil Barrett, John Varvatos, Rogues Gallery, Rag & Bone  whose boots are up to scuff.