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Khaki pants (a.k.a. “khakis”) have had an unreliable reputation in their decades of existence. The trousers have reached pinnacles of culture, being called “American classics” and “icons” of menswear.

Even the best khaki pants for men can spark a bit of pre-teen PTSD: memories of getting “dressed up” for eighth grade graduation, some older cousin’s wedding, a friend’s bar mitzvah. At the time, you ...