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But few, if any, have been more enduring than the penny loafer, which became inextricably linked to American style after young people started stuffing pennies in the notched strap atop it.

“You also want the back of the shoe to be firm.” When trying on penny loafers, they should be snug. “Leather will soften and stretch, but you don’t want to be clawing your toes to keep the ...