Are You Too Old to Wear Cool Sneakers?

We’re in a golden era for covetable sneakers. But at a certain age, should you move on from Nikes and Adidas? Plus: A guide to suitable trainers at any age

BEFORE ERIC APPLEQUIST and his wife embark on a night out, he stops and asks her one crucial question: “Is it okay for me to wear sneakers to dinner?” Most waking hours, the 37-year-old client strategist in Kansas City can be found in sneakers. “I try to get away with it as much as possible,” said Mr. Applequist, who is partial to colorful, covetable Nikes. “I dress pretty normal—jeans and a button-down and a sweater—and then I let my sneakers be my accessory.” But though this formula passes muster nearly anywhere he goes, as his pre-restaurant inquiry indicates, he still struggles with the question of sneakers’ appropriateness...