Minimalist, ultra-luxe brand The Row, founded by the ever-chic Mary-Kate and Ashley Olsen, recently debuted a pair of $690 rubber flip-flops, which has caused a stir among style savants.

Go ahead and wear your rubber sandals — even in New York City. By Casey Michael Henry Flip-flops have remained one of the most reviled men’s-wear items. Tom Ford regularly inveighs against ...