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A Little Fabric Goes A Long Way

Jack of Spades has kept a medium rise on all of its pants to combat the low-cut trend that is drowning the denim market. "We focus on fitting the body of a 40 year old, which separates us from many other companies," Ordioni explains. The higher waist makes for acceptable workplace attire when paired with a sports coat or dress shirt.

His khakis ($135) are The High Roller by Jack of Spades. His shirt ($125) is by Lenor Romano. His belt ($70) is by Johnston & Murphy.

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