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THE LOWDOWN
This effect is all about calculated casual, so tee shirts and knits should top his shopping list. Add color to his all-black-and-drab wardrobe--and replace any two-years-ago cargo pants lingering in his closet--by getting him into hip bright-hued bottoms. Now that leather's not just for the bold bad boy, he should swap that hide jacket for a so-now long pea coat. As far as shoes go, this look requires boots. Kalinsky suggests a military-inspired version or a slip-on ankle boot.
HOW TO SELL YOUR MAN ON THIS STYLE
He prides himself on his "I don't give a #!@%" garb and is loathe to look like a follower, so it's imperative you don't tell him to catch up ...