You can wear cufflinks with everything from your best business shirt to a ratty flannel work shirt. And yes, some people are doing the latter – never underestimate the contemporary hipster’s love for mixing high fashion with low. Practically speaking, most men will wear cufflinks in business and relatively formal social settings, as an accent to a suit-and-tie ensemble. That said, more relaxed links are perfectly acceptable with a sports jacket, and can add an air of playfulness that simple buttons don’t provide. There are no hard and fast rules. Wear cufflinks when you want to wear cufflinks. The only limits are your collection of suitable shirts.