Though Settles’s “old man’s wallet” consists of a rubber band around a roll of bills, watches are his accessory Achilles’ heel. This hard-to-miss Breitling wristwatch is from Time & Time Again on Newbury Street. “I’m pretty loud with my ties,” says Settles, who favors unusual color mixes and bold patterns. This Hickey Freeman silk tie is from Saks Fifth Avenue in Boston.